By Michael Slezak
Updated June 22, 2007 at 07:24 PM EDT

My all-time favorite episode of Starting Over involved a woman who was asked to sit inside a cardboard box, write down her “issues” on its walls, and then bust her way to the outside as a way to “break down her barriers.” Because there are no cardboard boxes in the blogosphere, we can’t reenact that stupendously stupid-beautiful moment today, but I’ve cooked up an exercise that elicits a similar reading on the pop-cultural shame-o-meter. Here’s what I want you to do: Take a few minutes to peruse your iPod song list — or paw through your CD collection — and then share the five most shameful songs in your collection. And remember, I wouldn’t ask you to dive into the humiliation pool if I wasn’t already standing in the deep end, arms outstretched, promising to buy you a pony. Ready… set…jump!

(1) Samantha Fox (pictured), Naughty Girls (Need Love Too) Stop judging me! This track was downloaded from a compilation CD called Ladies of the ’80s; you, on the other hand, have no excuse for knowing all the words to the chorus.

(2) C-Note, Wait Till I Get Home No joke, I might be out of a job by day’s end if my boss watches the corresponding video clip at YahooMusic, especially the part where these cut-rate Backstreet Boys bust vaguely obscene moves while delivering the line “bring it on home, daddy.” Oh, how I wish I were making that up.

(3) Lita Ford, Hungry The musical equivalent of a late-night movie on Cinemax, but 57% less artful.

(4) Patra, Pull Up to the Bumper Purchased at the iTunes store in the last 30 days, but in my defense, I’d been drinking a little bit.

(5) Scatman John, Scatman (Shi-Ba-Bop-Ba-Dop-Bop) This will be blaring from the speakers when I begin my descent into music hell. It burns! It burns!