What’s the biggest musical misstep by an artist you usually adore? One of mine is “Tall Cool One” by Robert Plant.
Fitter, Happier by Radiohead.
California English by Vampire Weekend.
Both feature heavy vocal distortion and are flies in the ointment of otherwise brilliant albums. IMO.
Moved from IMHO to Cafe Society.
Kokomo - The Beach Boys
I Just Called to Say I Love You - Stevie Wonder
I wouldn’t necessarily say that I adore him, but…
The Life of Chris Gaines, by Garth Brooks
Any time that the Rolling Stones let Keith “sing”.
But, but…**Happy **and **Before They Make me Run **are excellent!! I’d go with **Their Satanic Majesty’s Request **by the Stones as a misstep before…
How about **Chris Cornell’s **(Soundgarden) album with Timbaland? Cornell is regularly held up as the best voice in rock over the past 20 or so years - even the stuff with Audioslave charted 
- but his stuff with Timbaland was a complete change in direction and flopped hard. Just youtube “Chris Cornell Timbaland” and there are most of the tracks. Just Cornell’s voice over pop/r&b beats without his grunge howl used…
The song from the movie Beaches (Wind Beneath My Wings). I don’t know if Bette Midler wrote it, or someone else did. But there’s one bit where she’s singing FLYYYYYYYYYYY and sliding around from note to note.
The first time I heard this, it was sung at a military retirement dinner. I thought the singer (someone’s wife) was merely botching the song.
Then I heard the original… and it was just as awful. It sounded like the singer couldn’t figure out what note to hit. Honestly, it sounded OFF KEY. Which was a shocker, from a singer of Midler’s calibre. Ugh.
The album “By the Way” by the Red Hot Chili Peppers. The most interesting bass line on that album is less interesting than the least interesting bass line on any of their previous albums.
Two from Bowie - Shake It from Let’s Dance, and the 1974 butchering of John, I’m Only Dancing.
(Note: the original 1972 John was an awesome song. It’s the 1974 disco version that’s an abortion.)
911 is a Joke as covered by Duran Duran
The longest musical misstep surely has to be Bob Dylan’s in the 1980s.
I generally agree but I like Can’t Stop.
How about La Diva, the disco album by Aretha Franklin?
Urgh.
We haven’t gotten to rappers: how about **Ice-T’s **move to metal with Body Count and the infamous song Cop Killer? Or **Lil’ Wayne’s **move into rock right before he went to jail that went nowhere?
At least partially redeemed by their excellent cover of Hey Joe. Ice T’s delivery adds a sort of believeability to the lyric…
U2’s Pop
Led Zeppelin’s “Hats Off to (Roy) Harper”
R.E.M.'s Around the Sun
Any non-live Metallica album after Garage, Inc.
Morrissey’s Maladjusted
Cold Lake by Celtic Frost. The band that basically invented extreme metal try to sound like Def Leppard. Not particularly good (to say the least), and not included in the reissues of their albums.
Rolling Stones “Their Satanic Majesties”
Jethro Tull “A Passion Play”
Elvis Presley “Old McDonald had a Farm”
Cheap Trick “All Shook Up”
Lou Reed “Metal Machine Music”
Chris Gaines
The Jam breaking up/formation of the Style Council
The Clash Cut the Crap
MC5 Back in the USA (the production, not the songs)