Episode: Gypsies, Tramps and Weed; 2000
Cher as Cher calling out Jack for loving his Cher doll a little too much — yes, please!
Episode: Dolls and Dolls; 2003
Yaaas Queen (of pop)! We were living for that time Madge flexed her funny bone and popped up on the series playing Karen's delightfully quirky roommate, Liz.
3. Britney Spears
Episode: Buy, Buy Baby; 2006
Speaking of LOL-worthy cameos, Brit Brit turned up her southern charm and southern accent for her turn as Amber-Louise (THAT NAME!). Ms. Amber-Louise was recruited to play Jack's conservative co-host on his OutTv talk show Jack Talk. And you can it bet it wasn't just Jack who was giving us the giggles this episode.
4. Jennifer Lopez
Episode: I Do, Oh, No, You Di-in't; 2004
When Karen decides she wants to marry Lyle, the only person fitting enough to perform at her wedding is J.Lo, naturally. A fab performer for a fab lady is what we always say. She reprised her role in the Season 7 premiere, FYI: I Hurt, Too that fall, setting up a cameo for another diva in the following episode(*).
5. Janet Jackson(*)
Episode: Back Up, Dancer; 2004(**)
No, actually do make a big fuss. It's Janet or Miss Jackson, if you're nasty.
6. Elton John
Episode: The Honeymoon's Over; 2002
You know who runs the gay mafia? Elton freaking John.
7. Hall and Oates
Episode: The Definition of Marriage; 2006
Speaking of pitch-perfect wedding performers, two years after J.Lo, the dynamic duo stopped by to see Grace and James (Taye Diggs) off into holy (green card) matrimony.
8. Barry Manilow
Episode: Fanilow; 2003
The cameo (he played himself) that reminded us that we're all Fanilows at heart.
Here's to hoping the crew finds themselves in equally ludicrous situations with some equally-incredible pop stars in the future. Might we suggest: