Singles of the '00s, Part 1: Rap/R&B Crossover

Last year, as the '00s or the Aughts or whatever we're calling them were coming to a close, I prepared a series of posts here, with lists of my favorite albums and singles of each year of the decade. By the end of the year, I had counted down my 100 favorite albums of the decade. And I always wanted to do a similar list for singles, but I decided to put off that undertaking for a while, partly because I knew there was no way I'd be able to limit myself to just 100. After a few months of procrastinating, I decided on a different format: several lists of 50, divided up into genres. There'll be a rock list and a pop list, but since the overwhelming majority of my favorite singles of the last 10 years were hip hop and/or R&B, I decided to make a few different lists for those, including one for just all of the many gray areas in which both are involved.

R&B and soul music and almost every other kind of music has been in hip hop's DNA pretty much since its birth, but it's been a very gradual road to the two of them becoming distinct but inextricably connected commercial forces. Pretty much every "rap station" in the country plays mostly R&B songs and rap songs featuring R&B singers. R&B singers themselves have been thugging and jacking hip hop slang since the early '90s heyday of Jodeci, Bel Biv Devoe, and the rise of long-running superstars R. Kelly and Mary J. Blige. Rappers have been increasingly relying on sung hooks, whether sampled or provided by R&B singers or even singing a little themselves, to sell their records pretty much since "It Takes Two." And in the past decade, pretty much every kind of crossover between hip hop and R&B has happened, often resulting in some of the worst music ever made. But I'm gonna try to concentrate on the good songs here. I'm also going to try a new format: counting down all 50 songs throughout this week, 10 a day from Monday to Friday. You can bookmark this post and come back to it as I add new songs, or you can follow me on Twitter and get updates when I add new ones. Here we go!

50. Kanye West f/ T-Pain - “Good Life” (2007)
#7 Hot 100, #3 Hot R&B/Hip Hop Songs, #1 Hot Rap Tracks

T-Pain didn't start the fire, but he's fanned the flames a lot the past few years. In 2005 the failed Florida rapper stumbled onto a successful career as an R&B singer after starting to toy with AutoTune pitch correction technology and named his debut album Rappa Ternt Sanga. Within a couple years, everyone in hip hop was calling him for hooks, and within a couple more years they'd bought their own AutoTune plugins and every other rapper started turning into a singer. The Grammy Award for Best Rap/Sung Collaboration, which was created in 2002, gave two nominations to tracks featuring T-Pain in 2008. But the remarkable part is that he was the sung part on one song, "Good Life," and the rap part on the other, Chris Brown's "Kiss Kiss." The better of those two hits is itself a microcosm of Kanye West's tendency toward both R&B crossover and opulent displays of starpower: "Good Life" features co-production from both DJ Toomp and Timbaland, and in addition to T-Pain's hook and a Michael Jackson sample, Kanye grabs two other platinum singers, Ne-Yo and John Legend, to sing for a couple seconds each at the end of one of his verses.

49. Lil Mo f/ Fabolous - “4Ever” (2003)
#37 Hot 100, #13 Hot R&B/Hip Hop Songs

Here's the first of several appearances that both of these artists make on the list, together and apart. They had their first hit together, and then a couple more, and have probably done half a dozen tracks together in total. I always loved the way this is kind of a frilly, girly song about marriage, but the beat bangs hard as fuck, this coulda been a hit for any rapper, love that stuttering guitar stab. Fab's always been admirably willing to just jump on any R&B song and not sound embarrassed or half-assed, he stays on topic and comes up with some funny lines, does his 16 bars and dips out. He may never get props from hardcore heads for that, but I think that's kinda dope and unique.

48. Cee-Lo - “Closet Freak” (2002)
#99 Hot 100, #56 Hot R&B/Hip Hop Songs, #22 Hot Rap Tracks

And here's our first solo performance on the list from a one-person rap/R&B fusionist. Although his Dungeon Family brethren Andre 3000 scored perhaps the biggest singing rapper hit of all time with "Hey Ya!" (which, spoiler alert, probably should be on this list but isn't, because I don't like the damn thing), Cee-Lo is by far a more capable singer and juggler of genres. He'd already been appearing on Common albums as a hook singer and not a rapper for a few years by then, but it was still kind of a trip to turn on BET Rap City one day in 2002 and see the cat from Goodie Mob doing this crazy Funkadelic homage video. I like how he basically raps one verse at the beginning, and then spends the whole rest of the song vamping and chanting and crooning. Cee-Lo would go onto much greater success later in the decade, writing and producing Tori Alamaze's "Don't Cha" (which ended up being the Pussycat Dolls' first hit), and then forming the regrettably named group Gnarls Barkley and singing the megahit "Crazy" (which, spoiler alert, also isn't on this list). But I still feel like "Closet Freak" is the seminal moment where Cee-Lo tipped his hand at what he was really all about.

47. Jay-Z f/ Alicia Keys - “Empire State Of Mind” (2009)
#1 Hot 100, #1 Hot R&B/Hip Hop Songs, #1 Hot Rap Tracks

For most of his career, Jay-Z was one of the few rappers of his era who could score solo hit after solo hit without the aid of an R&B singer. One of his first singles featured Mary J. Blige, but the relative disappointment of the R&B-heavy singles for his second album, 1997’s In My Lifetime Vol. 1 and the huge success of the practically R&B-free hits from 1998’s blockbuster Volume 2: Hard Knock Life seemed to give him the confidence to trust his ear for other kinds of hooks. He’d sample little orphan Annie and loads of ‘70s soul records, let producers like Pharrell sing hooks here and there, do 2 albums with R. Kelly and loads of guest spots on girlfriend/wife Beyonce’s records, but when it came to solo singles, he almost never relied on R&B singers from 1998 to 2008 (the few that were featured on minor hits, Mashonda, Chrissette Michele and Static Major, were relative unknowns who didn’t even appear in the videos). So it was a little bit funny when last year, months after “Death Of AutoTune” made Jay’s disgust for rappers singing and relying on singers for hits more explicit than it’d ever been, he finally bit the bullet and let R&B superstars Rihanna and Alicia Keys co-headline two consecutive singles that ended up being among his biggest chart hits ever. “Run This Town” was a relatively bland tough-guy record that seemed to get by mostly on the collective momentum of Jay, Ri and Kanye being on one song, but “Empire State of Mind” was a certified monster both commercially and critically, as his first solo #1 on the Hot 100 and the Village Voice’s Pazz & Jop poll. And it came at an appropriate time: Jay’s long deteriorating rapping skills had finally gotten to the point where nobody who likes this song actually enjoys the verses, and it’s pretty much universally agreed that the Alicia Keys parts carry the whole song.

46. The Roots f/ Musiq Soulchild - “Break You Off” (2002)
#99 Hot 100, #55 Hot R&B/Hip Hop Songs

In addition to their niche as the sole prominent instrument-playing band in mainstream hip hop, The Roots have long occupied a weird halfway point between hip hop purism and the kind of tuneful, accessible rap'n'bullshit that their fanbase rarely tolerates from other types of hip hop artists. Maybe it's just that they associate with the classy neo-soul singers, like Erykah Badu and Raphael Saadiq, maybe it's just that their R&B-tinged singles were so good that it didn't matter. But for a while there they were in a good groove with these soulful lead singles gaining them what little radio airplay they've ever gotten, "Break You Off" being the last of them before the failure of 2004’s ill-advised Scott Storch faux-banger "Don't Say Nothin'" cleared the way for the band to abandon all pretense of trying to get on the radio and just played to their base with every subsequent single release.

45. Truth Hurts f/ Rakim - “Addicted” (2002)
#9 Hot 100, #2 Hot R&B/Hip Hop Songs

When Dr. Dre signed Rakim to Aftermath at the beginning of the decade, it was one of the most hyped up unions in hip hop history, a legendary MC and a legendary producer teaming up for an album that could never live up to expectations and ended up not existing. One of the only songs that came out of that era, and certainly the only one that impacted the charts, was Ra’s perfectly foreboding verse on an R&B one hit wonder’s one hit, sinking his immediately recognizable voice into the unfamiliar terrain of an Indian sample (later the subject of a lawsuit) looped up by DJ Quik. I can still remember how the song seemed to come out of nowhere that summer and was instantly in heavy rotation.

44. Drake f/ Trey Songz - “Successful” (2009)
#17 Hot 100, #3 Hot R&B/Hip Hop Songs, #2 Hot Rap Tracks

Even Drake’s biggest fans will admit how much his rapping owes to both Lil Wayne and Kanye West, but people don’t talk about how his much ballyhooed singing voice (which, to be honest, is just aight, good for a rapper, etc.) is also the product of mimicry. The first few times I heard Drake’s breakthrough solo hit, “Best I Ever Had,” I coulda swore Trey Songz was singing the hook. The first few times I heard the follow-up, “Successful,” I figured Drake’s Trey impression was so consistent that it was him singing the hook, when it was in fact Trey this time. Trey Songz had been bouncing around the industry for a few years, seemingly singing hooks for every rap album that would have him, even multiple appearances on LPs by no-names like Ebony Eyez, just to get his name out there, before he finally started to break through as a major star last year. And part of that breakthrough came because one of the no-names he’d been doing songs with all that time, Drake, was himself starting to become popular. I guess his budget hook singer strategy kinda worked. Also, note that I’m listing the single version, not the original mixtape version with the terrible Lil Wayne verse and extra Drake lyrics, or the video version with the superfluous Trey verse. And also please note this amazing sentence from the song’s wikipedia entry: “Accompanied by a dark tone, the songs lyrics contain quips of self-determination.”

43. DJ Khaled f/ Akon, T.I., Fat Joe, Rick Ross, Birdman and Lil Wayne - “We Takin’ Over” (2007)
#28 Hot 100, #26 Hot R&B/Hip Hop Songs, #11 Hot Rap Tracks

On some level, I feel like songs like this where rappers outnumber singers by a 5-to-1 margin almost don’t count, it’s just a rap posse cut. But at the same time, I’d feel like one of those people who refer to Akon as a rapper if I didn’t include it. And really, I do want this list to include some hard rap anthems that feel like they just kinda happen to have a singer involved.

42. Big Punisher f/ Donell Jones - “It’s So Hard” (2000)
#75 Hot 100, #19 Hot R&B/Hip Hop Songs, #11 Hot Rap Tracks

There was nothing novel about being a big fat motherfucker doing suave R&B joints in the wake of Biggie (note the great “One More Chance” reference in this track), but it was clear that Big Pun worked well in that lane, from “Still Not A Player” to the J.Lo joint. And even though “It’s So Hard” just happened to be the last single he released while he was alive, and is kind of a catchy, lighthearted song, the way the ended up shooting the video after he died, with a bunch of cameos of stars mouthing Pun’s lyrics and somberly holding up lighters, gave the song this weird mournful quality that still sticks with me whenever I hear it.

41. Nivea f/ Lil Jon and the Youngbloodz - “Okay” (2004)
#40 Hot 100, #14 Hot R&B/Hip Hop Songs

When I first heard “Put Yo Hood Up,” I thought Lil Jon’s voice and production aesthetic made for one of the harshest, most aggressive sounds I’d ever heard on mainstream rap, and I never would’ve guessed that a few years later, it took just one big crossover hit, “Get Low,” to get R&B acts to start calling him to put his gang shouts and screaming synths on their tracks. His first big R&B production, 2004’s “Yeah!” by Usher and Ludacris, turned into arguably the biggest hit of the decade, and the next, “Goodies,” was another chart-topper that launched Ciara’s career. Neither are on this list because, even as I’m trying to accurately build the canon and tell its story here, I just don’t really like those songs and I think the whole crunk’n’B trend, though it’s had a huge impact on pop music and influenced a lot of great singles since then, really took a while to not sound terrible to my ears. So in my weird contrarian brain, Nivea’s tardy entry into the crunk’n’B sweepstakes, “Okay” (which according to Wikipedia was recorded before “Goodies” and held back by the label, but was heard by the public much later), is my favorite track out of that whole weird period. Three years after writing "Okay," Terius “The-Dream” Nash wrote what proved to be one of the biggest rapped/sung collaborations of the decade, Rihanna and Jay-Z’s “Umbrella” (SPOILER ALERT: it’s not in this list either – I’m actually dissing 3 megahits in this entry!), and launched his own fairly successful solo career. At the time of “Okay,” though, he was Nivea’s husband and a relative unknown, but you can already hear a lot of his signature tics in this track.

40. Diddy f/ Keyshia Cole - “Last Night” (2007)
#10 Hot 100, #7 Hot R&B/Hip Hop Songs, #25 Hot Rap Tracks

Sean Combs, no matter what you call him, is the single most instrumental figure in the merging of hip hop and R&B over the past 20 years. In his early days as an A&R and producer, he was responsible for roughing up Mary J.’s sound and smoothing out Biggie’s sound, and at the height of Bad Boy’s peak of taking hits from the ‘80s and making them sound so crazy, no sample was too soft or too melodic (or too obvious). Diddy’s forthcoming album, Last Train To Paris is being looked at as some kind of Johnny come lately addition to the AutoTune rap’n’bullshit canon, but let’s give credit where credit’s due: his heart is obviously in this soft batch R&B rap game. Nearly every song on 2006’s Press Play featured R&B guest singers, including all four singles. And the biggest of them, “Last Night,” had Diddy himself singing a sad little song of lost love over a chunky, glitzy, Prince-sampling beat, with Keyshia belting all over it but still essentially just singing backup to the main artist, almost two years before Kanye’s musically and thematically similar 808s & Heartbreak.

39. Jagged Edge f/ Nelly - “Where The Party At” (2001)
#3 Hot 100, #1 Hot R&B/Hip Hop Songs

Nelly is probably the single most shamelessly tuneful rapper of the pre-AutoTune era, so I knew he had to pop up on this list, but for a while I wasn’t sure where. If I counted any of his solo hits, it’d start a slippery slope for any rapper who delivered a sing-song chorus, and of his duets with singers, my favorite is “Over and Over” with Tim McGraw, which is a country/rap crossover, no R&B. But this little gem was and is a banger, sometimes I forget how fun it is.

38. Pharrell f/ Jay-Z - “Frontin’” (2003)
#5 Hot 100, #1 Hot R&B/Hip Hop Songs

Like Nelly, Skateboard P presented some dilemmas for me as for his presence on this list. Obviously he’s a producer first, but performed vocals on many, many of his hits, sometimes rapping, sometimes singing, often somewhere in between. So I made the judgement call that his hooks on rappers’ songs, even the ones where he’s really belting out, like “I Just Wanna Love U (Give It 2 Me)” and whatnot, don’t count, partly because there are so many great ones they’d clutter up the list fast. But his debut solo single, where he was in straight up crooner mode, definitely counts. At the time, his falsetto was already starting to get kind of old, but that hook was undeniable and the plush simplicity of the beat fucking killed. Even Hov’s half-assed 8 bars are perfect for what they are.

37. Mary J. Blige f/ Method Man – “Love @ 1st Sight” (2003)
#22 Hot 100, #10 Hot R&B/Hip Hop Songs

2003’s Love & Life is the only flop, or at least the closest thing to it, in a career that’s been remarkably consistent in terms of sales and hits, and it’s possible that high expectations are to blame. On the heels of the massively successful No More Drama, Mary enlisted Diddy to exec produce her next album for the first time since the one-two punch of What’s The 411? and My Life that launched her career, and reunited with Method Man for a lead single that would reprise the pairing that produced arguably the best and biggest hip hop/R&B collaboration of the ‘90s, his “I’ll Be There For You/You’re All I Need To Get By.” In that context, sure, “Love @ 1st Sight” can’t help but feel like a disappointment, but I’ll stand up for it as probably my 2nd favorite Mary single of the decade, for the way it takes the usual ‘90s rap sample retread (in this case Tribe’s “Hot Sex On A Platter”) and actually does something with it, layering some melodic keys over the chorus in a way that interacts nicely with the vocal hook, while Meth goes all out deploying his usual effortless charisma on what would prove to be pretty much his last appearance on a major radio hit to date. I thought about including another Mary single, "Enough Cryin'," on this list, since it features her rap alter ego Brooke spitting a verse ghostwritten by Jay-Z (intended to be rapped by Foxy Brown before she started going deaf), just because it would be interesting in the context of the list, but that song is kinda garbage.

36. Ghostface Killah f/ Ne-Yo - “Back Like That” (2006)
#61 Hot 100, #14 Hot R&B/Hip Hop Songs, #11 Hot Rap Tracks

Ghostface has always seemed to have a special affection for soul music, beyond all the samples in those Wu Tang beats, that comes from being a part of the last generation of rappers that's old enough to remember music before rap. It never really manifested itself in any way that benefited his career, though, and his R&B themed album last year Ghostdini was a commercial and critical flop. This was one point, though, where he got on a song with a contemporary R&B singer and got a hit, but it all still felt kind of in his wheelhouse and captured his basic appeal. And just like "Love @ 1st Sight" was the last moment of heavy radio rotation for his Wu Tang homey Meth, "Back Like That" was the last time Ghost would ever touch the charts.

35. Snoop Dogg - “Sensual Seduction” (2007)
#7 Hot 100, #5 Hot R&B/Hip Hop Songs, #10 Hot Rap Tracks

Here we are, the only solo performance on the entire list. Just as Diddy’s singing turn (albeit with help from an actual singer) anticipated the deluge of similar efforts from rappers that would follow, Snoop Dogg’s AutoTune single, which at the time seemed to be a late addition to the growing ranks of mostly singers using the vocal effect in the aftermath of T-Pain (Chris Brown, R. Kelly, etc.), actually turned out to be not just ahead of the curve of other rappers, but a much more confident and singular effort than anything that came out of the army of AutoTuned raps that followed. And I'd like to think that that's because Snoop, like Ghostface, has a strong relationship with soul music, and that even this seeming modern bandwagon-jumping is just a chance to him to pay tribute to his '70s funk and R&B influences. That's born out by the playfully retro video, with Snoop appearing to be singing through a vocoder despite the fact that the song is clearly done with AutoTune, which highlights the double duty he’s pulling by depicting Snoop the singer and Snoop the rapper as completely distinct characters. This song is also remarkable for being one of the only clean radio edits ever where the single version of the title and lyrics just works better and sounds way better than the album version, "Sexual Eruption."

34. Shade Sheist f/ Nate Dogg and Kurupt - “Where I Wanna Be” (2000)
#95 Hot 100, #60 Hot R&B/Hip Hop Songs, #2 Hot Rap Tracks

Somewhere, Shade Sheist is next to Knoc-turn'al on a special milk carton reserved for West coast rappers that briefly got some mainstream exposure and some big name co-signs in the past decade, but somehow never got it together to get as famous as goofy-ass Game. For one summer, though, Sheist had a blazing summer jam with possibly the sunniest hook in Nate Dogg’s long line of gangsta hits.

33. Bobby Valentino f/ Lil Wayne - “Tell Me” (2005)
#51 Hot 100, #13 Hot R&B/Hip Hop Songs

I wrote a lengthy post here 2 years ago about the long winding path Lil Wayne took to becoming the go-to guest rapper of choice for R&B singers everywhere over the course of his career, and I won’t regurgitate any of that here. Although Destiny’s Child’s 2004 single “Soldier” is often thought of as the beginning of a lot of things (Wayne and T.I. being looked at as the two biggest southern rappers, Wayne on R&B songs, Wayne being embraced by the Jay/Beyonce camp), I feel like Wayne didn’t really settle into the kind of groove of duets with young male R&B singers until this track a few months later, which cleared the way for more hits with Chris Brown, Lloyd, etc. Plus it’s a pretty dope song.

32. Kanye West f/ Syleena Johnson - “All Falls Down” (2004)
#7 Hot 100, #4 Hot R&B/Hip Hop Songs, #2 Hot Rap Tracks

The original version of the song (titled “Self Conscious” on the advance version of College Dropout) sampled one of the few hooks from Lauryn Hill’s legendarily awful Unplugged album, and I’m sure Kanye, always one to try and make everything into a big event, probably hoped to get Lauryn to officially appear on the single release, or at least clear the sample, which would’ve been a pretty big co-sign for him at that point in his career. But she didn’t, so Kanye re-recorded the hook with a C-list Chicago R&B singer, the song was a hit anyway, we all stared as Stacey Dash’s ass throughout the whole video, and the rest is history.

31. Justin Timberlake f/ The Clipse - “Like I Love You” (2002)
#11 Hot 100, #53 Hot R&B/Hip Hop Songs

I remember sitting on the couch in my old Parkville apartment with some college friends, watching the ‘02 VMAs when Justin debuted this song. I’d loved the R&B direction of ‘N Sync’s last couple singles “Gone” and “Girlfriend” and was totally rooting for Justin to make the big crossover with his solo career, and I quietly fumed while all my friends snorted derisively at him that night. In retrospect the song probably wasn’t the right first step forward and the performance was a little weak, so I understand why “Cry Me A River” (which I don’t like nearly as much) was what really kickstarted mass adult music fan acceptance of Justin, and led to the same friends bumping Justified at a party maybe a year later. This song rules, though, and it always cracks me up to think how hard the Clipse still cling to their street cred when they were on a Backstreet Boys remix and a ‘N Sync solo record so early in their career.

30. Fabolous f/ Mike Shorey and Lil Mo - “Can’t Let You Go” (2003)
#4 Hot 100, #2 Hot R&B/Hip Hop Songs, #2 Hot Rap Tracks

I already covered the other Fab/Mo hit that came out simultaneously with this one, and this feels like a little less of a true collaboration: Fab's boy Shorey (who, as far as I know, never did anything with his career besides sing hooks on Fabolous songs) sings the main chorus, and Mo is just kinda there to shadow it, "Hot Boys"/"Put It On Me"-style. It's really one of the most lyrical girl songs of all time, though, the internal rhymes are crazy on lines like "there'll be a clip tossed if I go back/ with stains of your lip gloss on my throwback," Fab at his most emotionlessly monotone while actually putting a fair amount of humanizing detail into it. And that beat's so soft it took me months to realize or admit that it was Just Blaze. Definitely check the very underrated the remix, though, where Blaze puts on a harder beat and Fab rewrites every line of the song with a gangsta twist.

29.Lil Jon & The Eastside Boyz f/ Usher and Ludacris - "Lovers & Friends" (2004)
#3 Hot 100, #2 Hot R&B/Hip Hop Songs, #1 Hot Rap Tracks

It was interesting how Lil Jon’s highly anticipated Crunk Juice, though by no means a commercial disappointment, not only failed to produce another “Get Low”-style club banger but didn’t even seem to try, instead opting to release two gang shout crunk anthems as the initial singles, and then follow those up with the wimpiest slow jam possible. Lil Jon, Usher and Luda were never going to equal the success of “Yeah!” but I have to say I enjoy this song a lot more, as goofy and maybe even campy as it is. Each of them takes a verse, and each one is entertaining in its own right: Usher vamping it up hardcore with big emotional high notes, Luda adopting a goofy slow flow but still meticulously in the pocket of the beat and inserting some warmth and humor into the premise of the song, and then Lil Jon, seemingly only doing any vocals just because this was, after all, for his album, and grunting through an uncomfortable 16 bars that’s at turns tender and at turns some of the most vulgar shit he’s ever said on record: “are you sure you wanna go this route? / let a n$&%@ know before I pull it out.”

28. Faith Evans f/ Missy Elliott - “Burnin’ Up” (2002)
#60 Hot 100, #19 Hot R&B/Hip Hop Songs

Even though it’s known now that Timbaland and the Neptunes go way back, and have collaborated and worked with artists from each others’ respective camps many times now, there was a weird moment for a couple years at the beginning of the decade when the 2 biggest producers in pop music were from the same place, were constantly compared to each other, but seemed to kind of ignore each others’ existence and stay completely seperate. Not saying anyone ever thought there was beef, it was just kind of odd. So in a weird way, it actually felt like a big deal to hear Missy on a Neptunes track in 2002. Also this song is fire, and the Just Blaze remix with Freeway is killer too.

27. Ne-Yo f/ Peedi Crakk - “Stay” (2005)
#36 Hot R&B/Hip Hop Songs

When Def Jam signed the songwriter behind Mario’s “Let Me Love You,” and issued a debut single featuring the great but not particularly famous Puerto Rican rapper Peedi Crakk, I took it to mean one of two things: either Ne-Yo wasn’t a very big priority at the label, or he was Latino and the label was just pairing him up with one of the only other Latinos on the label for some Roc-La-Familia synergy (obviously, I hadn’t seen a picture of Ne-Yo or anything when I first head this song). I was wrong on both counts, and I was also wrong to quickly dismiss the song as lightweight, and found its kinetic, upbeat charms growing on me more and more once it was released on Ne-Yo’s debut In My Own Words. The song was kind of a flop (you’ll note it’s the only one on the list so far that didn’t crack the Hot 100), and obviously his career didn’t really kick off until “So Sick” a few months later, but now I hear DJs play it all the time and it’s always welcome.

26. Dr. Dre f/ Snoop Dogg, Nate Dogg and Kurupt - “The Next Episode” (2000)
#23 Hot 100, #11 Hot R&B/Hip Hop Songs, #9 Hot Rap Tracks

Like “We Takin’ Over,” it kind of feels wrong to put this song on the list since it’s essentially a posse cut rap song with a tough guy singer on the hook. But again, it’s a classic, it needs to be represented, gotta give Nate Dogg his props.

25. Akon f/ Styles P. - “Locked Up” (2004)
#8 Hot 100, #6 Hot R&B/Hip Hop Songs

When Akon debuted with this song a few years ago, he seemed like a gangsta R&B hook man in the Nate Dogg mold, with a gritty backstory including prison time and a collab with another ex-con from The Lox helping him tell the world his story. And for a while, he stayed in that lane, with the follow-up “Ghetto” and hooks on similarly gritty singles by Young Jeezy, Obie Trice and, once again, Styles P. Since then, though, Akon’s convict image has been discredited by the Smoking Gun and he’s staked his hitmaker reputation on sunnier, cheesier hits for the likes of Gwen Stefani and Lady Gaga, and the idea of him as a successor to a badass like Nate Dogg seems like a joke.

24. Keri Hilson f/ Lil Wayne - “Turnin’ Me On” (2008)
#15 Hot 100, #2 Hot R&B/Hip Hop Songs

Wayne’s willingness to do any R&B feature that came his way, which was refreshing in 2005, had become kind of wearying by the time of Tha Carter III, mostly because every singer in the fucking industry took him up on it. This was the last it really came out dope, though. The original mix of the song is also notable for Wayne introducing the “miss Keri, baby” ad lib, which Hilson herself then started using as her own signature on the final version and other songs, and which I now can’t hear without thinking of it as “miscarry baby.”

23. Kanye West f/ Dwele - “Flashing Lights” (2007)
#29 Hot 100, #12 Hot R&B/Hip Hop Songs, #2 Hot Rap Tracks

It's interesting how Dwele's kind of quietly become the go-to hook singer lately for Kanye, who can and has worked with just about every star in R&B. I guess he needed someone kind of low key and not too expensive to help flesh out his tracks that just needed a little singing but not necessarily a big star feature ever since John Legend went and got huge. I think Kanye having a good working relationship with many R&B singers is why his shitty singing on 808s & Heartbreak pissed me off so much, he coulda just made a dope R&B album with the right collaborator instead of that mess.

22. Ryan Leslie f/ Cassie and Fabolous - “Addiction” (2008)
#35 Hot R&B/Hip Hop Songs

Of Fab’s many, many recent R&B features, this is one is probably my favorite, and in general he’s just displayed a great chemistry with R-Les, who produced a couple joints on his last album and the single by Slim from 112 that he was on. Leslie's singing career hasn't been all that successful, and there's part of me that hopes he just focuses on producing for rappers, it seems like a strong suit for him.

21. Ciara f/ Missy Elliott - “1, 2 Step” (2004)
#2 Hot 100, #4 Hot R&B/Hip Hop Songs

As I’ve said in other entries on the list, I was never a big fan of “Goodies” or crunk’n’B in general, but I always kinda dug the lighter, brighter variations on the sound. People love to hate on Jazze Pha, and he is kind of an unctuous motherfucker, but really he made some great-sounding radio jams and I think was better suited to the whole dirty south R&B crossover thing than Lil Jon.

20. Snoop Dogg f/ Justin Timberlake and Charlie Wilson - "Signs" (2005)
#46 Hot 100

This song was released almost immediately after the Janet incident at the Super Bowl, and even though the backlash against Justin in the black community seemed to have pretty much blown over by the time of FutureSex/LoveSounds, I strongly suspect that sentiment was the reason this song completely flopped on R&B radio (note that it’s the only song on this list with no placing on the Hot R&B/Hip Hop Songs chart). Because seriously, listen to this song, it’s a fucking hit, it should have been everywhere. I’ll also lay some blame on the far inferior “Let’s Get Blown,” for squandering the spot as the immediate follow-up to “Drop It Like It’s Hot” that should’ve rightfully belonged to “Signs.” This is also probably my favorite collaboration between Snoop and the Gap Band’s Charlie Wilson, who’ve been touring and recording together since way way back in the Death Row days, just another sign of Snoop’s old school R&B head status.

19. Lil Bow Wow f/ Jagged Edge - “My Baby” (2003)
#42 Hot 100, #17 Hot R&B/Hip Hop Songs, #15 Hot Rap Tracks

The decade's archetypal kiddie rapper built his empire on R&B collaborations as much as anyone this side of Ja Rule, with Jagged Edge-assisted singles on each of his first three albums, and later a career resurgence with hits featuring Chris Brown, T-Pain, then-boo Ciara, and Omarion, who he linked up with again for an ill-fated teenybopper answer to Jay-Z and R. Kelly’s Best Of Both Worlds. The oft-overlooked track that I’d pick as his secret classic, though, is this JE heartbreaker about the girl Bow Wow loves that’s stuck in an abusive relationship with another guy. It’s mostly the swaying, tender chorus that gets to me about this song, and the video, which fleshes out the story and makes it a little more over the top and tragic, but as a piece of storytelling this is one of Bow Wow’s (ghostwriters’) finest moments. If you ever want to know what the most embarrassing song I’ve ever teared up to is, seriously, it’s probably this.

18. John Legend f/ Andre 3000 - "Green Light" (2008)
#24 Hot 100, #6 Hot R&B/Hip Hop Songs

The Love Below was a bunch of bullshit to me, and I spent most of the decade thinking Andre was pretty much a lost cause, so far gone up his own critically-acclaimed ass that he’d rather break genre boundaries that don’t need breaking than making good rap music. In the last few years he started to hit the guest MC circuit hard, though, and even if that half dozen or so verses he dropped ended up being kind of overrated, there were still some great songs in there, one of my favorites being this fantastic dancey R&B jam that’s so far beyond what he ever would’ve come up with on his own, but added just the right energy to.

17. Jennifer Lopez f/ Ja Rule - "Ain't It Funny (Murder Remix)” (2002)
#1 Hot 100, #4 Hot R&B/Hip Hop Songs

One of the key ingredients of the ‘90s hip hop soul boom was the pairing of singers with tracks borrowed from the previous decade’s hip hop classics, whether it was Mary J. singing over “Top Billin’” drums or “This Is How We Do It” jacking a Slick Rick beat. By the beginning of the ‘00s, though, occasional homages turned into constant, lazy retreads, with the weakest singers and most uninspired songs enlivened by beloved samples from ‘90s rap classics. The worst practitioner of the trend was Irv Gotti, who built much of Murder Inc.’s house of hits by raiding Bad Boy’s back catalog for every hot beat he could find. And when he ran out of Biggie beats to plunder, he even recycled his on one true mid-‘90s classic beat, Jay-Z’s “Can I Live,” for a mediocre Ashanti single. Still, even the most cynical hack is gonna make a jam here and there, and Ja waxing enthusiastic about J.Lo’s ass over the “Flava In Ya Ear” beat is the hit I’d save from those dark, dark times in R&B radio. Incidentally, it was J.Lo who took the biggest PR hit for sample jacking out of this whole trend a year later over “Jenny From The Block,” when the Trackmasters (perhaps the era’s most shameless beat biters after Irv) lifted the flute hook the Beatnuts made famous on “Watch Out Now” and JuJu and Psycho Les were able to pull her card for screwing some fellow NY Latinos with a song trumpeting her roots. Of course, the actual flute part is from an Enoch Lite record, which was properly credited, which shows just how fuzzy all these issues of appropriation are, and ultimately it’s more about what records people associate particular sounds with. I should also note here that I'm generally avoiding remixes (especially since almost every R&B hit gets a remix with a rapper these days) except in cases like this, where the remix is such a big hit that it pretty much eclipses the original.

16. Keyshia Cole f/ Missy Elliott and Lil Kim - "Let It Go" (2007)
#7 Hot 100, #1 Hot R&B/Hip Hop Songs

Five years after the era of Irv and J.Lo, practically every big Notorious B.I.G. track had been recycled by someone or another, but somehow “Juicy” had been relatively untouched, and when it finally was reused on a new hit, Keyshia and Missy actually did right by the track. Missy’s meta instructions to DJs (“they gon’ mix it with Biggie – ‘it was all a dream!’”) were a little too cute, a little too on the nose, but in the context of this breezy summer jam it kinda worked anyway.

15. Joe f/ Mystikal - “Stutter (Remix)” (2001)
#1 Hot 100, #1 Hot R&B/Hip Hop Songs

Here goes another homage to a ‘90s chestnut, but it’s a more subtle one. Where “Ain’t It Funny” and “Let It Go” paraded their origins proudly, “Stutter” simply takes the organ loop from Pharcyde’s “Passin’ Me By” and surrounds it with a completely different and decidedly production style, and a dramatically different type of rapper (if still an equally animated MC). I’ve known some people who characterize “Stutter” as a pure beat jack that gets by only on nostalgia, but I really love this song on its own merits and hear the comment musical element completely differently in its new context: on the Pharcyde song, the organ sounds like an organ, but on the Joe track I always process it as some kind of icy sci-fi soundtrack whir to match its state-of-2001 surroundings, which include vaguely IDM-ish zipping synths and stu-stu-stuttering vocal edits. Also, another remix that was way way bigger than the original.

14. Lil Mo f/ Fabolous - "Superwoman Pt. II" (2001)
#11 Hot 100, #4 Hot R&B/Hip Hop Songs

Fab’s first taste of fame, and the best of his holy trinity of Lil Mo collab hits. That beat is just the fuckin’ illest, I don’t have anything else to say.

13. Justin Timberlake f/ T.I. - "My Love" (2006)
#1 Hot 100, #2 Hot R&B/Hip Hop Songs, # Hot Rap Tracks

Timbaland and his then-new protege DanjaHandz cementing their new rave synth aesthetic and pop radio dominance, Justin coming back from that maybe-post-Superbowl R&B backlash I mentioned in the “Signs” entry with a vengeance, and T.I. hitting his stride as a suave ladies' man superstar. Also the highest of three appearances by Justin on the list, the highest of two for Danja, and somewhat amazingly, the first (but not last) appearance by Timbaland, not counting his minor contributions to “Good Life.”

12. Lloyd f/ Lil Wayne – “You” (2007)
#9 Hot 100, #1 Hot R&B/Hip Hop Songs

And now, the highest of Lil Wayne’s 4 appearances on the list. I always loved how subtle the Spandau Ballet interpolation on this is, at least to my ears, it was nagging at me in the back of my brain for a few weeks before I realized where I recognized the melody from. The outright sample of “True” on the remix almost kinda spoiled the trick for me.

11. Ludacris f/ Bobby Valentino - "Pimpin' All Over The World" (2005)
#9 Hot 100, #5 Hot R&B/Hip Hop Songs, #2 Hot Rap Tracks

It’s funny, I haven’t been listening to many of the songs on the list this week, because they’re pretty much all tattooed on my brain permanently. But this is the first one that just thinking about and trying to write about made me want to listen to it, and I pulled it up on YouTube and danced around the room with my son to it, so I know I’m getting way up towards the good stuff. I love Luda’s flow on this, it’s simple and straightforward but with this conversational ease and rhythmic swing that makes me feel like he’s channeling the Fresh Prince or maybe even Slick Rick. And even for a song with “pimpin’” in the title there’s this weird warmth and innocent happiness seeping through the whole thing, just a perfect summer jam. The D.C. Go-Go band Rare Essence picked up on that swing brilliantly with their remix of the song, and Luda actually performed the song with them at the VMAs that year, which was just amazing. The highest of 2 appearances each for Bobby V. and Polow Da Don.

10. Young Jeezy f/ Akon - “Soul Survivor” (2005)
#4 Hot 100, #1 Hot R&B/Hip Hop Songs, #1 Hot Rap Tracks

In late '05, Jeezy already had a ton of buzz and strong and it wasn't really clear if he was gonna be a successful singles artist -- I really believe the whole Gucci Mane beef over "Icy" wouldn't have popped off if Jeezy wasn't afraid his album didn't have any crossover hits on it. But doing a kind of dark R&B record with Akon, who at the time was still the "Locked Up" guy and not a weird corny fraud, was really the perfect move that cemented both of them as radio staples.

9. Young Gunz f/ Rell - "No Better Love" (2004)
#36 Hot 100, #15 Hot R&B/Hip Hop Songs, #11 Hot Rap Tracks

Neef and Young Chris were not especially clean cut or charismatic, but in a group alongside Beanie Sigel and Freeway, just not having neckbeards was enough to make them State Property’s token pinups who’d cover the R&B demographic. And their big lead single off their debut album, following the kinda shitty faux-old school “Can’t Stop, Won’t Stop,” was a big cavernous banger with a great hook delivered by Rell, the forgotten soul man who’d been waiting for Roc-A-Fella to give him another shot at a hit since that song on the Streets Is Watching soundtrack and would never get another one again.

8. Plies f/ Ne-Yo - "Bust It Baby Pt. 2" (2008)
#7 Hot 100, #2 Hot R&B/Hip Hop Songs, #2 Hot Rap Tracks

Hip hop/R&B songs don’t always, but frequently do, play off of the rough/soft contrasts implicit in such collaborations. And just as Ja Rule’s thug love songs were the most extreme and successful formula of the first half of the decade, certified goon Plies and his lengthy string of slick melodic hits were the second half’s equivalent. And the contrast was never more ridiculously heightened than here, with Plies grunting disgusting come-ons like “my favorite panties of yours are the ones that’s see-through” while Ne-Yo croons sweet nothings like “I do everything I can to prove I’m a better man than your friends think I am” over a saccharine ‘80s Janet sample. I’m still waiting for them to realize how great a duets album would be and make The Year Of The Goontleman.

7. Mya f/ Jay-Z - "Best of Me Pt. 2" (2000)
#55 Hot R&B/Hip Hop Songs

I like to think that when Jadakiss started going at Jay-Z and Roc-A-Fella in 2001, piling onto the whole Nas beef, some of his resentment may have stemmed from the fact that a year earlier, just as his solo career was getting started, he had two big features on records by platinum R&B artists, and both of them were upstaged when Jay hopped on remixes of both (the other being R. Kelly’s “Fiesta”). The Jada/Swizz version technically charted higher, but I’ve barely heard the original on the radio in years, whereas the Jay/Trackmasters version gets spins every damn day still. In pretty much every collaboration with Beyonce, Jay’s been controlled and distant, usually rapping about how great he is even when she’s singing about how passionate her love for him is, but contrast that with the blithely funny, R-rated intimacy of lines like “my hand’s up your skirt, goddamn you flirt/ what’s a little me on top gon’ hurt?/ maybe a little, but pain is pleasure and pressure bust pipes/ and you look like the ‘I like it rough’ type.” He had a point, too, Mya really does give off that vibe.

6. Fabolous f/ Nate Dogg - "Can't Deny It" (2001)
#25 Hot 100, #13 Hot R&B/Hip Hop Songs, #11 Hot Rap Tracks

It’s funny to think that Fab, a classic NYC punchline rapper who later mastered the art of Southern crossover, kicked off his career by straight West coastin’ with Nate Dogg singing 2Pac lyrics over a Rick Rock beat.

5. Missy Elliott f/ Ludacris - "One Minute Man" (2001)
#15 Hot 100, #8 Hot R&B/Hip Hop Songs

A decade ago, blurring the line between rapping and singing was primarily the province of female artists like Lauryn Hill and TLC and of course Missy, and this is one of her biggest singles in which she pretty much sang the whole thing and left the rapping to the guest. When “One Minute Man” first dropped as the follow-up to “Get Ur Freak On,” I regarded as part of an overall pattern in Missy’s career up to that point, with the more ‘safe’ and accessible R&B flavored 2nd single proceeding after the bolder, more offbeat lead single (“Sock It 2 Me” after “The Rain,” “Hot Boys” after “She’s A Bitch.”) Over the years, though, I’ve come to like this song more than “Freak,” for its killer vocal melodies, one of Timbaland’s most subtle virtuoso productions (that big goofy 3-note keyboard hook flowing into a variety of sneaky countermelodies, the percussive guitar strum punctuating every fourth bar), and one of Luda’s great early star turns, not to mention Trina’s great verse in the video version and Jay’s even better one on the remix.

4. R. Kelly featuring T.I. and T-Pain - "I'm A Flirt (Remix)" (2007)
#12 Hot 100, #2 Hot R&B/Hip Hop Songs, #1 Hot Rap Tracks

In the early-mid ‘90s, R. Kelly, along with Jodeci and Nate Dogg, helped introduce the R&B thug paradigm, guys that can sing but are often closer to hip hop in terms of image and lyrical content. And in the ‘00s, R. shed whatever degree of Disney-friendly “I Can Believe I Can Fly” public image he had and became as controversial and eccentric and scary to middle America as any rapper. Still, some of his biggest hits, no matter how many rappers they featured, were essentially bouncy, loping piano pop songs that sounded more like “Bennie and the Jets” than any other contemporary hits (which is somewhat appropriate when you keep in mind that “Bennie” was Elton John’s first hit to cross over to the R&B charts). This song is notable for having originated as a Bow Wow track, before R. decided to take it for himself, and since both versions got the same Billboard entry, it ended up topping the Rap Tracks chart even though the overwhelming majority of spins were for a version with an R&B singer as the main artist. It also represents, along with R.’s appearance on the “I’m N Luv (Wit A Stripper)” remix, his kind of passing the torch to T-Pain, who for a second was kind of looking like the next Kells, before he fell the fuck off. This is the highest of 3 entries on the list for T.I., the highest of 2 for T-Pain, and amazingly the only entry featuring R. Kelly, whose best ‘00s singles were surprisingly rarely with rappers (he had some dope songs with Jay-Z but no classics in my opinion, and a lot of the rappers featured on his own singles were, like, Big Tigger and The Game).

3. LL Cool J f/ Marc Dorsey - "Luv U Better" (2002)
#4 Hot 100, #1 Hot R&B/Hip Hop Songs, #2 Hot Rap Tracks

LL is in the history books as more or less the inventor of soft batch love raps, or at least the guy who made it a sustainable career model, but few of his many hits in the "I Need Love" mold are considered among his best up there with the “Mama Said”s and “I’m Bad”s. That the unbilled and relatively unknown Marc Dorsey sings the hook instead of Pharrell is a huge asset to this song being one of the Neptunes’ finest R&B-flavored works, with a beat that’s at once ethereal and aggressive, a wash of dreamy keys interrupted every couple bars by an abrupt three-note synth guitar stutter. The first time I heard this song, a mix show DJ was running the intro back a few times, so all I’d hear was that swirling, dramatic beat and LL intoning “this is hard to say, I wanna make sure I go about this in the right way,” and I thought it was gonna be some kind of epic, weird Neptunes street banger. I was mildly disappointed when I realized it was a girl song, but quickly got over it when I realized what a great one it is. “Luv U Better” is the kind of song about mature, long-term relationships that you rarely get in rap, especially from older married rappers who are afraid acting their age could kill their career, and LL's performances oozes a kind of passionate sincerity that he's never captured in any of his action movie or sitcom work, so much that even when he notes “I know you don’t feel appreciated, and whatnot,” as if rolling his eyes at and placating his significant other, it still feels like he’s pledging a renewed devotion that becomes more convincing with each verse. The highest of 5 Neptunes productions on the list.

2. Twista f/ Kanye West and Jamie Foxx - “Slow Jamz” (2003)
#1 Hot 100, #1 Hot R&B/Hip Hop Songs, #1 Hot Rap Tracks

A lot of the songs on this list, as much as I love them, can be thrown into one of two categories, sometimes both: mushy love songs and shrewd commercial moves. But there were hip hop artists who engaged with R&B in a way that was both arch and affectionate, none more than Kanye. It makes a certain kind of sense that his first big emergence from crate-digging producer to guy who gets to actually rap on hit songs was with such a meta celebration of soul music, but it's really Twista, another rapper who seems to love rhyming over shamelessly schmaltzy soul beats for reasons that go far beyond their commercial viability, that takes this from a cute novelty to an all-time classic. I can still remember how excited I got about this song the first time I heard it, on an early DJ Drama tape (when he was still "DJ Dramatic" and wasn't on the south's dick yet) where it was mislabeled as "Her Favorite Song (Gonna Be)" for some reason. A few weeks later, some savvy Atlantic A&R plucked it from The College Dropout advance that had been bouncing around Def Jam's release schedule throughout 2003, made it Twista's lead single and it shot to #1, vaulting both Chicago rappers into the mainstream simultaneously and setting the stage for a comedian’s unlikely crossover as an R&B star.

1. Ja Rule f/ Lil Mo and Vita - "Put It On Me" (2000)
#8 Hot 100, #2 Hot R&B/Hip Hop Songs, #11 Hot Rap Tracks

To many, Jeffery Atkins Represents Unconditional Love Exists represents everything that went wrong with hip hop and R&B collaborations in the '00s -- that cookie monster growl bellowing corny cliches at female duet partners over pillowy slow jam beats and samples jacked from better songs. But through all the Rule 3:36 singles and those J.Lo remixes, I really think he was making some great radio records that embraced the R&B element of his music in a way that his more cynical contemporaries and enemies never bothered to (there are a hell of a lot of 50 Cent songs that technically could be on this list, but aren’t). Rule belted out the chorus to this song all by himself on the original album version, although it didn't actually become not just listenable but incredibly catchy until Lil Mo came in and shadowed his every word to sweeten it up. The Murder Inc. formula didn't really go to shit until they tried replacing Mo's delirious melisma with the expressionless monotone of Ashanti as Rule's melodic foil a year or two later. This'll probably get more hated than any other ranking on the list, but I don't care, it's a fuckin' classic.
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