The Doobie Brothers are one of those rare bands who had success in two distinct eras with different lead singers, like AC/DC or Van Halen. But instead of their first frontman dying young or abruptly splitting with the rest of the band, the Doobies had an odd transitional period. Founding singer/guitarist Tom Johnston, who wrote and sang the majority of songs on their first 5 albums, had to take some downtime due to exhaustion and a stomach ulcer, and Michael McDonald stepped in help the band finish a tour, and wound up fronting the band for their next 4 albums (the 1983 live album The Farewell Tour offers a little glimpse of what it was like to hear McDonald perform Johnston tracks like "Listen To The Music"). But Johnston stayed in the band with McDonald for a few years, playing on 2 of the McDonald-fronted albums. When the band reformed with Johnston in the late '80s for Cycles, which contained their last top 10 hit "Doctor," McDonald co-wrote one deep cut, "Tonight I'm Coming Through (The Border)." And now both singers are back in the band for the Doobies' 50th anniversary tour, or would be, if they hadn't had to indefinitely postpone it. 

McDonald's by far the more famous Doobies frontman, thanks to their biggest album Minute By Minute and his subsequent solo career, but their tenures are pretty close to equal in terms of overall hits, with the Johnston era having a slight edge. A writer I'm friendly with once wrote a joke listicle of the best Doobie Brothers songs that was just "What A Fool Believes" 45 times in a row, which really irritated me and gave me extra motivation to do a deep cuts playlist and really appreciate their whole '70s/'80s run, because this series is really about not boiling acts down to their biggest hit. 

Guitarist Patrick Simmons is the only person who's been in every Doobie Brothers lineup, and he was kind of the second string lead singer in both the Johnston and McDonald eras. He sang their rocked up arrangement of The Art Reynolds Singers gospel song "Jesus Is Just Alright," but his signature song and the band's first #1, "Black Water," was kind of a surprise hit -- the first two Johnston singles from What Were Once Vices underperformed, but DJs started flipping one of the records over and playing the b-side. The Simmons songs on this playlist are "South City Midnight Lady," "Clear As The Driven Snow," and "Neal's Fandango," and Simmons and McDonald both sing on "Rio" and "One By One." Everything else is Johnston or McDonald, except "Busted Down Around O'Connelly Corners" and "Precis," which are instrumentals.

In my mind the Doobie Brothers kind of form a triptych with Steely Dan and Little Feat. All three bands were favorites of my father that I heard a ton growing up, and Michael McDonald recorded with all three. Jeff "Skunk" Baxter was a member of both the Doobies and Steely Dan, and the Doobies shared a producer (Ted Templeman) and label (Warner Bros.) with Little Feat, who they toured with on multiple occasions. The Doobie Brothers didn't have a dedicated keyboard player on their early albums, so most of the piano and organ on the pre-Michael McDonald records is by Little Feat's Bill Payne, including major contributions to hits like "China Grove" and "Jesus Is Just Alright," and Payne has been touring with the Doobies as a full-time band member since 2015. I consider Steely Dan and Little Feat to be two of the best bands of the '70s, if not the very best -- by comparison, I think The Doobie Brothers are a little less essential a little more middle of the road. But again, I really grew up on their songs and enjoy the hell out of them. 

Like a lot of '70s bands, The Doobie Brothers' first greatest hits compilation far outsold any of their proper albums -- 1976's Best Of The Doobies has sold over 10 million copies over the years, even though it just had the first couple Michael McDonald-sung singles and was released before some of his biggest songs with the band. Oddly, they had enough Hot 100 hits to fill an LP by that point, but the comp still included some non-singles, including "Rockin' Down The Highway" (which became one of the band's more popular songs over time) and "South City Midnight Lady" and "Without You" (which did not, but were live staples). 

I think they kind of hit a sweet spot in that middle period -- my favorite albums are Stampede, the last album under Tom Johnston's first era of leadership, and Takin' It To The Streets, the next album and the first with Michael McDonald. Stampede in particular has some really impressive stuff like "Music Man," which had horns and strings arranged by Curtis Mayfield, and "Rainy Day Crossroad Blues," which had guitar by Ry Cooder. "Neal's Fandango" features probably Jeff "Skunk" Baxter's best guitar solo outside of Steely Dan's "My Old School." And Takin' It has "Rio," which is very polyrhythmic and has a cool section with a few bars in 5/4. 

It occurred to me that the cover of their 3rd album, The Captain And Me, which featured a photo of the band under a freeway overpass that was broken apart by an earthquake, would've been a more apt (if on-the-nose) cover for their 7th album, Livin' On The Fault Line. Michael McDonald co-wrote "You Belong To Me" with Carly Simon -- after the Doobies released it on Livin' On The Fault Line, it became a major hit for Simon, and has since been covered by Anita Baker, Jennifer Lopez, and others.