Henry Rollins I think once said that there are no such things as guilty pleasures. WELL BULLSHIT MISTER ROLLINS I say. With music especially, I'm sorry, but there are songs and groups that you know in your head to be kind of pants (sorry to PANTS!) but who are nevertheless super hooky or singalongable or otherwise have that... something that makes you say "oh man, I have to listen to this band RIGHT NOW".
I will say that I think there ought to be a distinction made between things that are recorded for giggles and with the direct attempt to be ironic and uber-cool. I will grant you that the very first song on my little list here almost breaks that but it's so corny in its own right that I think it still passes. I'm not really looking for the musical version of Sharknado here, I'd prefer to see actual, good faith attempts at music that are kind of awful but singable: the sorts of songs you'd turn off immediately once they come on, but if you can't get to the media player of your choice in time you will soon sing along with.
A couple of mine:
Save Ferris: Come On Eileen
Yep, right from the middle of the ska era. Yep, I totally owned this album. And yep, I sure as hell listened to it so much that I can probably sing along with the entire thing even now.
Black Hole Sun... by Steve and Eydie?
Off the Lounge A Palooza album. Soooooo corny, it comes all the way back around the corny continuum and back into cool and then continues back along into corny once again. "Neath the black the sky looks DEAD".
Mel Torme: The Goodbye Look
Look. Mel is probably my favorite jazz singer, like, ever. Sinatra is bigger and brassier and just generally filled with more "cool", it's true (and also he gets extra points for the "hey guys, if I say "let's fly" instead of "let's sex" then even old people will listen to my music), but Mel is just so... unintentionally silly so much of the time you can't help but love the guy. This song is a cover of a Steely Dan song, backed by a big band, and features lots and lots of scatting. Yes, it is all of those things and it is awesome.
I will spare you all Lou Bega (even though, truth be told, I kind of love swing and the swing revival).