Episode 175 of "Will and Grace"
s08e05 The Hole Truth

The day before Will’s charity auction and carnival, Jack meets and begins dating Baby Glenn (guest star Jason Biggs), who is still riding his fifteen minutes of fame from when he got trapped in a hole for three days in the eighties. The two "celebrities" agree to be auctioned off for charity - Baby Glenn’s fans spend over a thousand dollars, but Jack begins to question his own notoriety when no one bids on him. Meanwhile, Karen just can’t force herself to break up with Malcolm (guest star Alec Baldwin), so to soften the blow she recruits Grace to be his date to the carnival. But Grace can’t stand his weird quirks and clingy personality and finally makes Karen confront him.