Tom Verlaine - "Yonki Time"
Lou Reed - "Chocolate Egg Cream"
Echo and the Bunnymen - "Ballyhoo and Bedbugs"
The Beatles - "Birthday"
OMD - "Bloc Bloc Bloc"
David Bowie - his cover of "Pablo Picasso," Tin Machine's cover of "Working Class Hero"

Prince - "Annie Christian" (he's done a lot of other stupid songs, but this one in particular has always bugged me)
David Bowie - "The Laughing Gnome"
The Police - "Mother"
The Beatles - "Don't Pass Me By"

1) "Every Day I Write the Book" - Elvis

2) A whole bushel of Neil Young and Dylan albums/tunes

3) More obscurely: Blur's entire Great Escape album (If Benny Hill collaborated with Martin Amis on a mid-90's britpop album, the results wouldn't be dissimilar.)

My Ding A Ling - Chuck Berry.

'Nuff said.

"My Ding a Ling" is a stupid song, no question about it ... but I'm confident that Chuck knew it all along. I doubt that most of the other artists listed in this thread (so far) knew that the songs they were laying down would end up in the "stupid" category. Some of them, I suspect, still don't see it.

One of Prince's biggest faults, as an artist, is that he has lacked a rigorous editor, internal or otherwise. Time and again, he has apparently believed that any idea he has must be worth pursuing. As much as I love Prince, I gotta say, it just ain't so.

I was thinking of a version of "Can't Help Falling In Love" by Elvis Presley that was done live in Vegas in which he flubs up the lyrics big time and laughs at himself. Also, even though it's an album rather than a song, #50 on Ira's list also strikes me as being pretty stupid (the King's own Metal Machine Music)

P.S.: Ironically enough, "My Ding-A-Ling" pipped out Elvis' "Burning Love", his last great single, out of the #1 spot back in '72

great plains - "why do punk rock guys go out with new age girls"
which is/was true. so, on a superficial level, that's deep.

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I love Yonki Time!!!!! I had 2 little kids when that album came out, and it was their favorite song.
Elvis the C doing his crooning bit is hard to take.