Okay, so I have “Toxic” and “Crazy” on my mp3 player, but I’m not embarrassed about those.
I am embarrassed to have “The Macarena”, “Major Tom” by Peter Schilling, “Low” by Flo Rida, and both versions of “Numa Numa” on my computer…
…but the only thing that makes me feel silly on my mp3 player is the song “Gay Boyfriend” by the Hazards. Well, that and “Girlfriend” by Aviril Lavinge.
I have several Britney Spears songs, including “Toxic,” and a couple T.A.T.U. songs too. Actually, I have a genre called Lame Pop that includes those, songs by Nine Days, The Backstreet Boys, Savage Garden, Blessid Union of Souls, Semisonic and Five For Fighting. Plus single tracks by Hillary Duff, Evan and Jaron, and Eagle Eye Cherry. I make up for that two hour chunk of my MP3 collection with the other 340 hours 
I am about to leap into the lead here:
The Spaniard Who Blighted My Life by Bing Crosby
Me, too. I have a good handful of them. Maybe we can start a support group?
The worst? Hmm. Well, it’s tough to embarrass me, I like a wide enough range that even some of the songs that pop on that make friends give me the old :dubious: look, I simply smile at them and ask if they’d prefer something else. I love punk (the Clash, NOFX), gay disco (PSB, Scissor Sisters), disco (Gloria Gaynor, Yvonne Elliman), anyone from the Minty Fresh label (Komeda, Doktor Kosmos, the Prototypes), industrial (NIN, KMFDM), funk (Earth, Wind and Fire)classic pop, current pop/R&B/some rap/etc (I love that Estelle song with Kanye, and I actually like and laugh my ass off at Black Eyed Peas), Britpop (Blur, Sleeper, Pulp), some 80s stuff (I heart Der Kommisar by After the Fire, the Smiths/Morrissey), J-Pop (hee), many foreign bands (Belle and Sebastian, Air, too damn many to name here)… so it’s tough to pick.
But the tunes I will turn red if someone catches me listening to?
Asereje - Las Ketchup
New Age Girl - Deadeye Dick
Annie, I’m Not Your Daddy - Kid Creole
Elton John is one of the most talented and accomplished artists of our time. Simon and Garfunkle are vastly underrated (particularly Simon) and many of their songs are on the soundtrack of my life. I don’t think there’s any reason to think of their music as embarrassing.
But if you mean you’re a hard rock guy and you enjoy an easy listening song now and again, well, that just makes you well rounded.
I have Miley Cyrus’ “See You Again” :o. And a Savage Garden song (“Break Me Shake Me”) as well as some awful J-pop. I’m pretty prone to earworms and they won’t go away unless I give in and listen to the whole song.
Sexbomb by Tom Jones.
Far too many to mention but here are a few ‘gems’ of embarrassments:
Crazy - Britney Spears
An entire album called ‘Invincible’ by a, now disappeared, boyband called Five given to me as a present
Cowboys und Indianer - a TERRIBLE German pop song got for novelty reasons and aprés ski nostalgia
Nothing’s gonna stop us now - Starship
Mr Vain - also got for novelty reasons/ sheer perversion of taste
Who do you think you are - Spice Girls
No matter what - Boyzone - it was part of a compilation album that had loads of GOOD stuff on it and two major turkeys like this and the next one
Love is all around - Wet, wet, wet - remember? From the film Four weddings and a funeral 
o:o:o
Disclaimer: but i have loads of cools stuff too - jazz greats, loads of heavy duty serious classical music, avant garde music, classics of rock and pop like Kate Bush, Kraftwerk, Radiohead, Pink Floyd just to mention a few
I can’t wait for his album. squeee
I’ve got lots of PDQ Bach. Lots and lots of it. That I will set up in playlists to go through several shows worth at once.
I’ve also got Clint Black’s Greatest Hits and Billy Joel’s Greatest Hits. And am a bit embarrassed to admit enjoying many of the songs from both those albums.
I’m not embarassed by the J-pop, though. That’s just fun. 
When ever the list of the 100 worst songs ever made is published my first thought is, gee someone stole all my mix tapes, in the days before the I-pod. Now I say somebody has accessed my playlists. I have you all beat.
Sunshine Day-BradyBunch Kids
ABBA
Lost in Love-Air Supply
How Deep is your Love-Bee Gees
Horse with no Name-America
Safety Dance
In a Big Country-Big Country
Sweet Pea-Tommy Roe
Year of the Cat-AL Stewart
Somewhere in the Night-Barry Manilow
Took the Last Train-Bread
Woman in Love-Barbara Streisand
Lady in Red-Chris de Burgh
Foolish Beat-Debby Gibson
Reminiscing-Little River Band
Lucky Stars-Red Sauce
Undercover Angle-Alan O’Day
And that is just the beginning!
Stars are Blind by none other than… Paris Hilton
And then worse part is that my boyfriend put that on there.
I’ve got ABBA on there too, but I think that one’s the worst.
What’s embarrassing about that. PDQ Bach rules.
I have some very nerdy music on my Muvo. Like the Picard song (Captain Jean-Luc Picard quotes set to techno music), System of a Down’s rendition of the theme from Legend of Zelda, Still Alive from the Portal video game, and The Device Has Been Modified (GLADOS quotes form Portal set to techno music). Also lots of They Might be Giants.
Probably the most embarrasing song on there, though, is Total Eclipse of the Heart. :o
Everything on my 'Pod would embarrass most of you. Though probably not as much as Doodoocaca embarrasses me.
Being that I recently loaned my mp3 player to my 12 year old daughter, pretty much everything she put on there… from the Jonas Brothers to the Naked Brothers Band to the soundtrack from A Goofy Movie…
Check oput who was performing in St Martin this past January!
Technically not on my iPod anymore, since it got demolished in a car crash (somehow fell out of my backpack at the scene, got driven over several times by emergency workers, then someone put it back in my car - you could see two separate tire tracks on the case). But they are on my iTunes:
Naked Brothers Band
Hannah Montana
High School Musical 1 & 2
Disney Princess songs
(CircleofWillis, we should start a club.)
Most embarrassing music of mine?
Probably “I’m the Man” by Anthrax (horrible, awful proto-metal/rap, to the tune of “Hava Nagila”). It was very late, I was tired, and feeling overly nostalgic, so I bought it on Amazon’s MP3 service. Worst $0.99 I ever spent.
“Convoy” by CW McCall it’s cute.
Please tell me you misspelled Saturday Night Fever before I feel really old…
