Not sure if this has been done. Searching for relevant terms turned up nothing.
1. The Smiths: "Heaven Knows I'm Miserable Now" (and about half The Smiths' oeuvre)2. The KLF Featuring Tammy Wynette: "Justified and Ancient"
― Kevin John Bozelka, Saturday, 5 May 2012 16:40 (fourteen years ago)
3. The Kinks: "Phenomenal Cat"
― Leslie Mann: Boner Machine (C. Grisso/McCain), Saturday, 5 May 2012 16:49 (fourteen years ago)
4. malcolm mclaren - madame butterfly
― madame boo berry (donna rouge), Saturday, 5 May 2012 16:51 (fourteen years ago)
5. walk on the wild side - lou reed
― give me back my 200 dollars (NotEnough), Saturday, 5 May 2012 16:53 (fourteen years ago)
6. the Who - Tattoo
― Tarfumes The Escape Goat, Saturday, 5 May 2012 17:13 (fourteen years ago)
7. Scott Walker - Jackie
― poxen, Saturday, 5 May 2012 17:28 (fourteen years ago)
Pitch-blackly so, but:
8. Jim O'Rourke - "Halfway To A Threeway"
― You Don't Throw Oranges On An Escalator (Deric W. Haircare), Saturday, 5 May 2012 17:50 (fourteen years ago)
two of my favorite things in a song.
9. Millie Jackson - Summer (The First Time)
― yo just a couple (Matt P), Saturday, 5 May 2012 18:00 (fourteen years ago)
10. Lou Reed - "A Gift"
― henry s, Saturday, 5 May 2012 18:12 (fourteen years ago)
11. Todd Rundgren - "Piss Aaron"
― henry s, Saturday, 5 May 2012 18:14 (fourteen years ago)
12. Frank Zappa - "Montana"
― henry s, Saturday, 5 May 2012 18:15 (fourteen years ago)
13. Harry Nilsson - "The Most Beautiful World in the World"
― Emperor Cos Dashit (Adam Bruneau), Saturday, 5 May 2012 19:00 (fourteen years ago)
14. Flight of the Conchords "Sellotape"
― humba (NZA), Saturday, 5 May 2012 20:49 (fourteen years ago)
15. Denim - I'm Against The Eighties
― Morrissey & Clunes: The Severed Alliance (PaulTMA), Saturday, 5 May 2012 21:52 (fourteen years ago)
16. Denim - The Osmonds
17. The Flaming Lips - Waterbug
― Touché Gödel (ledge), Saturday, 5 May 2012 21:54 (fourteen years ago)
18. Prince - The Beautiful Ones
― Exile in lolville (Alfred, Lord Sotosyn), Saturday, 5 May 2012 21:57 (fourteen years ago)
(Prince owns this category btw)
19. Bob Dylan - All the Tired Horses.
― Pat Finn, Sunday, 6 May 2012 00:16 (fourteen years ago)
20. Yung Humma ft Flynt Flossy - Lemme Smang It
― misty sensorium (Plasmon), Sunday, 6 May 2012 00:31 (fourteen years ago)
21. Wedding Present - Why Are You Being So Reasonable Now?
― bendy, Sunday, 6 May 2012 00:58 (fourteen years ago)
22. The National - Lemon World
― Dan Bejar? Amanda Lear? You're Welcome! (Dr. Joseph A. Ofalt), Sunday, 6 May 2012 03:01 (fourteen years ago)
23. Ween - Right to the Ways and the Rules of the World
― Ask The Answer Man (sexyDancer), Sunday, 6 May 2012 03:05 (fourteen years ago)
24. Queen - Bohemian Rhapsody
― some dude, Sunday, 6 May 2012 03:09 (fourteen years ago)
25. Ween - "Push th' Little Daisies"
good argument could be made 4 Ween owning this thread 2
― henry s, Sunday, 6 May 2012 03:13 (fourteen years ago)
26. Love's Lines Angles & Rhymes - The Fifth Dimension
― Dan Bejar? Amanda Lear? You're Welcome! (Dr. Joseph A. Ofalt), Sunday, 6 May 2012 03:34 (fourteen years ago)
good argument could be made for stfu about ween
― some dude, Sunday, 6 May 2012 03:35 (fourteen years ago)
27. T.Rex - Planet Queen
― Dan Bejar? Amanda Lear? You're Welcome! (Dr. Joseph A. Ofalt), Sunday, 6 May 2012 04:03 (fourteen years ago)
To pick just 5:
28. Nick Lowe - Rollers Show29. Nick Lowe - Little Hitler30. Nick Lowe - American Squirm31. Nick Lowe - Love Like a Glove32. Nick Lowe - All Men Are Liars
― Hideous Lump, Sunday, 6 May 2012 04:47 (fourteen years ago)
good argument could be made for stfu about ween― some dude, Saturday, May 5, 2012 11:35 PM (Yesterday) Bookmark
no you
― billstevejim, Sunday, 6 May 2012 08:33 (fourteen years ago)
33. Robyn Hitchcock - "Earthly Paradise" (prob. a lot of RH songs here too)
― Vini Reilly Invasion (Elvis Telecom), Sunday, 6 May 2012 09:46 (fourteen years ago)
34. Cheech Marin - "Born in East L.A."
― Three Word Username, Sunday, 6 May 2012 10:33 (fourteen years ago)
35. Ween - Baby Bitch36. Ween - Fluffy37. Ween - Spinal Meningitis (Got Me Down)
― ┗|∵|┓ (sic), Monday, 7 May 2012 00:04 (fourteen years ago)
38. Tenacious D - "Fuck Her Gently"
― suidavyvan eht nioj (Whiney G. Weingarten), Monday, 7 May 2012 00:20 (fourteen years ago)
This would be Go-Kart Mozart's wheelhouse, I'd say.
― mr.raffles, Monday, 7 May 2012 04:26 (fourteen years ago)
Oh damn! 39. Denim - "Synthesizers in the rain"
― poxen, Monday, 7 May 2012 04:40 (fourteen years ago)
40. Flight of the Conchords- 'Jenny'
― underleg aeroboots i have smithed (darraghmac), Monday, 7 May 2012 04:44 (fourteen years ago)
ITT: "Hilarity"
― like Joe Pasquale and Gandhi (Noodle Vague), Monday, 7 May 2012 06:39 (fourteen years ago)
41. Digital Underground, "Freaks of the Industry"
― The Reverend, Monday, 7 May 2012 06:46 (fourteen years ago)
Yeah, I stretched the hilarity point on the Marin track, but it's actually pretty gorgeous-sounding from the second verse on.
― Three Word Username, Monday, 7 May 2012 07:02 (fourteen years ago)
42. Flight of the Conchords "Carol Brown"43. Ween "Chocolate Town"
Ween definitely owns this thread
― guess it's Honker Burger tonight...#fml (frogbs), Monday, 7 May 2012 17:24 (fourteen years ago)
44. The Divine Comedy - My Lovely Horse
― Scary Move 4 (dog latin), Tuesday, 8 May 2012 10:22 (fourteen years ago)
45. Billy Bragg – Walk Away Renee
― Manfred Mann meets Man Parrish (ithappens), Tuesday, 8 May 2012 11:41 (fourteen years ago)