
Feature Photo: Anne Jacko from Portland, Oregon, USA, CC BY-SA 2.0 <https://creativecommons.org/licenses/by-sa/2.0>, via Wikimedia Commons
# 10 – Dangerous
To me, this song still feels like a relatively new Doobie Brothers song, even though it was released over 35 years ago. Time goes fast. “Dangerous” was written by Patrick Simmons and released on April 15, 1991, as a single from the Doobie Brothers’ album Brotherhood. The song was recorded in 1991 and produced by Rodney Mills. Featuring Simmons on lead vocals, the track centers on a motorcycle rider embracing risk and freedom on the open road, including a reference to Harley Davidson. The song also appeared on the soundtrack to the 1991 film Stone Cold.
# 9 – Evil Woman
This is another one of those classic Doobie Brothers deep cuts. The song first appeared on the legendary Doobie Brothers album The Captain And Me. The opening guitar riff rocks the roof of the house. There have been a lot of rock songs written with the title “Evil Woman,” but this is one of the best.
# 8 – Slippery St. Paul
This one always reminded me a little of “Black Water.” Of course, this one came first, as it was released on the band’s debut album, The Doobie Brothers. The album was released in 1971. This was placed as the second track in the album. Just take a listen to that guitar picking. If you know nothing about music and you hear this song right after the Doobie Brothers’ “What a Fool Believes,” you would swear it was two completely different bands.
# 7 – 8th Avenue Shuffle
It’s quite a jump from the last album to this one in terms of the band’s sound, but the vocals, guitar sound, and the group are still the same. This was always one of my favorite tracks from The Doobie Brothers’ Takin’ It To The Streets album. That Patrick Simmons’ guitar sound and vocals you could tell from a mile away.
# 6 – I Cheat The Hangman
Well, this one was kind of dark. Released on November 12, 1975, as the third and final single from Stampede, with “Music Man” on the B side, the song was written by Simmons and produced by Ted Templeman. Its story follows a man leaving the gallows, with Simmons connecting the idea to a ghost returning home after the Civil War without realizing he is dead, a concept that gave the record the feel of an old West ghost town. Jeff Baxter described the piece as being done in three parts, and that structure helped shape a recording built around guitars, piano, vocals, strings, bass, and drums. The single featured vocals by Simmons and Maria Muldaur.
# 5 – Angels & Mercy
It may be hard to believe, but the Doobie Brothers had not released a studio album with Michael McDonald on board in over 45 years. In 2025, the band released Walk This Road. I was completely blown away by how good this album is. But this album represents is the perfect balance between the original sound of the Doobie Brothers and the Michael McDonald years. The band is playing as well as they ever have, and the vocals are just killer. Songwriting is once again top-notch, and the second track on the album featured this Patrick Simmons song that will just knock you rock and roll socks off.
# 4 – Dependin’ On You
If you look back at the music that Patrick Simmons contributed to the Doobie Brothers, you’ll find the southern-sounding Simmons that we heard often during the early years, and then, of course, the soulful style that he turned to during the Michael McDonald years. Many fans are split between these two different periods, while others like myself love both of them. “Dependin’ on You” was released on July 25, 1979, as the third single from Minute by Minute, backed with “How Do the Fools Survive.” The track features backing vocals from the late Nicolette Larson and Rosemary Butler, Commercially, the single reached number 25 on the Billboard Hot 100, number 37 on the Adult Contemporary chart.
# 3 – Wheels Of Fortune
I remember the first time I purchased his album and threw it on my turntable. I could not believe the sound of the guitars and how they just kind of blew out of my speakers. It’s one of the best-sounding records I’ve ever bought. It was Michael McDonald’s debut, and the band sounded completely different. Yet on the opening track, front and center was the killer voice of Patrick Simmons.
# 2 – South City Midnight Lady
Whenever I have composed any sort of Doobie Brothers song list, this is the song that people always comment about. “South City Midnight Lady” stands as one of the most loved Doobie Brothers songs of all time. It was originally released on the album The Captain and Me. The album’s two biggest hits, “Long Train Runnin’” and “China Grove,” were so massively successful that they kind of overshadowed the gem “South City Midnight Lady”. But the real Doobie Brothers fans heard it, and they loved it.
# 1 – Black Water
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