What are the most embarrassing song(s) on your iPod?Why are they embarrassing? My answers
“I’ll Stand By You”-Pretenders (want it to be my wedding song) (guys aren’t supposed to think about stuff like that)
“Fields of Gold”-Eva Cassidy (reminds me of my celebrity crush) (ibid.)
Total Eclipse of the Heart (I think you know why this is embarassing).
Guys don’t like the Pretenders? I’ll let my dad know. He’ll be disappointed to learn he’s not allowed to think Chryssie Hynde is awesome anymore.
I’m not embarrassed by any of the music on my iPod. I think I should be embarrassed by “Asereje”, but I don’t care. I like it.
Merneith-I LOVE Bonnie, too!
I’ve all those on my I-pod and some air supply as well, but in a playlist called wuss rock, so that makes cool right 
Most embarassing is probably the entire Buffy musical…
Jesus Christ Superstar, original cast recording (not the movie) with Ian Gillan of Deep Purple/ Black Sabbath. Embarrassing because it makes people think I am either A) religious, which I’m decidedly not, or B) into Broadway musicals (not common or “cool” in my circle), which I’m also decidedly not, or C) old, which I…well, OK, I kind of have to own up to that one I guess.
Moved MPSIMS --> Cafe Society
twicks, who has nothing but great music on her iPod
My ex-fiancee was a major musical fan, and we had our iTunes accounts synced together, so I have several hundred cast recordings lingering in my iTunes that occasionally show up on my iPod. Lots of Mandy Patinkin.
When I first installed iTunes, I pointed it at my various music directories so it could collect everything together. I forgot that I had tried out one of those “erotic hypnosis” tracks on a lark years before and never deleted it… and it got put into rotation once when the ex was listening to my stuff at random. That was a bit embarrassing.
Probably “I’m On the Road” by The Partridge Family.
A couple that come to mind: Patty Duke: “Don’t Just Stand There” and C Company’s “The Battle Hymn of Lieutenant Calley”.
And while it’s not embarassing in the same sense, there’s enough X-rated live album patter on there that I had to stop playing rock selections on shuffle at work. Some might regard Iggy Pop bellowing “All right, fuckers!” at the crowd as unbecoming a professional environment. 
Lots of American Idol recordings from David Cook and Jason Castro.
Hootie and the Blowfish’s cover of “Hey Hey What Can I Do”.
I used to have a lot more hair metal on my old iPod, but my computer crashed and I got a new one and couldn’t get the stuff from the old one onto the new one.
Shared all with my wife too. Not sure which is worse, but they’re all [del]wincers[/del] winners:
Sound track to “The King And I”
All Disney music from every cartoon they’ve ever made
Anything Highschool Musical
“The Tikki Tikki Tikki Room” by Hillary Duff
Perhaps “Erase! Erase! The Power of Alt-F4 Compels Thee!!!” will be a voice comand on the next Itouch.
To be fair, I don’t mind Karen Carpenter once in a while though.
And I do accept full responsibility for The Wallace and Grommit Megamix
It depends on the crowd. I would cringe if something fey and New Age-y like The Angels of Venice came on when I’m around my friends, but I would likewise cringe if something obnoxious like the Laughing Hyenas came on when I’m around my parents and their friends.
Of course, I always cringe when Blue Öyster Cult or “(I Just) Died in Your Arms” by Cutting Crew comes on.
Ha, I have “Don’t Just Stand There” too! From the Greasy Kids and Teenage Dreams: Teen Rock Singles 1956-66 Liberty Records compilation that I bought on cassette and safeguarded like loose diamonds until I could convert it.
Yep, my gf and I have an agreement to be faithful to each other. My only out is that if Ms Hynde ever approached me and instigated a fling, I’m allowed to accept. Seriously.
I’m a dude. I have this on my iPod. It was my wedding song, by my suggestion, and I still cry like a little baby girl every time I hear it.
Don’t worry about what guys are supposed to like. Awesome f’ing song are awesome f’ing songs.
“A Man Without Love” by Englebert Humperdinck" because I’m not a 68 year old woman.
“I Woke Up in Love This Morning” by The Partridge Family, because I’m not an 11 year old girl. In 1974.
Actually 90% of the stuff on my Ipod has a high embarassment factor. What can I say; for some reason the stuff most conducive to working out is also a little on the geeky side. Obviously my first mention above isn’t a workout song; it’s just perty
Man Like Me by Robert Downey Jr. Bought because I had a raging crush on him, still on my iPod because I like having a definitive answer to this question.
I’ve got nothing but great stuff in my MP3 collection: Jim Nabors, Glen Campbell, the Doodletown Pipers…
Stuff I should be embarrassed by, I suppose, but I’m not 'cause I like it all unironically:
Britney Spears - “Toxic” and “Oops! I Did It Again”
Beyonce - “All the Single Ladies”
Frankie Smith - “Double Dutch Bus”
Kelly Clarkson - “Since U Been Gone”
I maintain that these are all good pop songs despite being teenybopper material.