Coolio died on Wednesday at the age of 59. His time in the spotlight was relatively brief, but he really made his mark in history, with "Gangsta's Paradise" being probably the first really serious street-oriented rap song to hit #1 on the Hot 100. Over the last couple decades he lived it up as a professional celebrity, doing things like publishing a cookbook and becoming the running mate for a porn star's campaign for president. But he was a major star of west coast rap's commercial explosion, with a couple of songs that will live forever, so I thought I'd dig a little under the surface of his catalog. 

1. It Takes A Thief 

2. Hand On My Nutsac

3. U Know Hoo! f/ WC

4. I Remember f/ J-Ro and Billy Boy

5. Smokin' Stix

6. Dial A Jam

7. Thru The Window

8. Rollin' With My Homies

9. Exercise Yo' Game f/ E-40, Kam and 40 Thevz

10. Is This Me? f/ LV and Rated R

11. For My Sistas

12. Get Up, Get Down f/ Malika, Shorty, Leek Ratt, P.S., WC and Ras Kass

13. Kinda High, Kinda Drunk

14. Homeboy f/ Montell Jordan

15. 2 Minutes & 21 Seconds of Funk

16. Hit 'Em f/ Ras Kass

17. Money (Dolla Bill Y'all)

18. Gangbangers f/ Daz Dillinger and Spade

19. What Is An MC

Tracks 1, 2, 3, 4 and 5 from It Takes A Thief (1994)

Track 6 from The Jerky Boys: Original Motion Picture Soundtrack (1995)

Track 7 from New Jersey Drive, Vol. 1 (Original Motion Picture Soundtrack) (1995)

Track 8 from Clueless: Original Motion Picture Soundtrack (1995)

Tracks 9, 10, 11, 12 and 13 from Gangsta's Paradise (1995)

Coolio moved to Compton as a kid and released his first single in 1987, the year west coast rap started to really take off with Ice-T and N.W.A.'s first albums. Coolio was a member of WC And The Maad Circle, who made an album in 1991, before WC became part of Westside Connection. And then in 1994, after Death Row had turned L.A. into the new center of the rap universe, Coolio got a solo deal and became a mainstream star with "Fantastic Voyage." 

I guess it makes sense that a soundtrack single became Coolio's enduring hit, because "Smokin' Stix" and two other songs from It Takes A Thief appeared in Poetic Justice before the album was released. And Coolio hit the soundtrack circuit hard after that first album, appearing on at least four soundtrack albums in 1995 alone. His contribution to Clueless, "Rolling With My Homies" inspired the very memorable "rollin' with the homies" dialogue in the movie, and it's a real '90s time capsule to see Coolio right between Green Day and Superchunk on the Jerky Boys soundtrack. It's just a shame Coolio's "Kenan & Kel" theme song never made it to streaming services, that's a banger.

L.V. from "Gangsta's Paradise" is one of those odd pop footnotes, a guy who sang the hook on one blockbuster song, but never really launched a career of his own after that, who was almost 40 at the time. He appeared on one deep cut on the Gangsta's Paradise album called "Is This Me?" and it's surprising they didn't drop more songs as a duo. It's fun to hear Coolio on tracks with west coast legends like E-40 and Ras Kass, or remake Jimmy Spicer's "Money (Dolla Bill Y'all)" for In Tha Beginning...There Was Rap, the compilation of covers of early rap songs best known for the Def Squad version of "Rapper's Delight." 

Public Enemy's Chuck D and Jay-Z were both 26 when their first albums were released, and are considered the classic examples of late bloomers in hip hop who were grounded by having lived a bit before they became stars. By comparison, Coolio was 31 when It Takes A Thief came out. He never necessarily posed as an OG or a veteran, but he had a certain no-nonsense air to him, even on uptempo songs. Coolio was really a versatile guy who could hang with the gangsta rappers or keep it light, whatever worked for the song. He became a crossover star without dancing around like MC Hammer, and continued carrying himself like a seasoned everyman rapper.

Coolio had the kind of 3-album career arc that was typical in hip hop's first couple decades: a hot debut, and even bigger second album, a follow-up that had a decent-sized hit, and then quickly dwindling fortunes after that. He had an album called Coolio.com released only in Japan in 2001, and then included a few songs from it on his next domestic album, El Cool Magnifico. He released 3 albums after that aren't on Spotify today. But it seemed like he lived a good life and got to really reach heights that not many rappers of his generations did in terms of chart success, and he had a great flow that always sounded perfect on big trunk-rattling G-funk beats. 

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