Grace 0, Jack 2000 is the 5th episode of the third season and the 51st overall.
Grace finds it hard to call it quits with Ben, whose charm makes her reconsider. Meanwhile, to save his failing cabaret act, Jack unsheathes his claws and writes nasty new material based on Will's private life.
Grace decides she doesn't love Ben and she should break up with him, but when she does so he refuses to let her. Finally, with help from Karen, Grace convinces herself that she does love Ben, but then Ben breaks up with her.
Jack has a new cabaret act, Jack 2000, which does terribly until he adds stand-up that makes fun of Will's personal life. Will is insulted, and stops telling Jack details about his personal life. Jack's act fails when he has no new material and he's depressed about his best friend being mad at him. Karen convinces Will to help Jack out, and Will gives Jack permission to use even his most embarrassing moments, but Jack, reminded of what a good friend Will is, doesn't use them.
- Eric McCormack (Will Truman)
- Debra Messing (Grace Adler)
- Sean Hayes (Jack McFarland)
- Megan Mullally (Karen Walker)
- Shelley Morrison (Rosario Salazar)
- Gregory Hines (Ben Doucette)
- Jason Stuart (Stuart)
- Troy Morton (Audience Member)
- Jeremy Forte (Heckler)
- Wil Bowers (Guy)
- This episode marks the last appearance of Gregory Hines in the series. Hines had planned to make a return to the show until he became sick in 2002. He would later die in mid 2003.
- The "duet" Jack sings with himself is "Mockingbird", a duet originally by Inez & Charlie Foxx.
- Learning that Will is about to tell about his encounter with the souvlaki vendor, Jack pretends to talk to an intercom and says "Miss Hathaway, hold my calls". This is a reference to Nancy Kulp's character in the sitcom The Beverly Hillbillies, who was a secretary.
- As Will scoots on his Herman Miller chair out of the office, he makes the Road Runner's meep-meep sound.
- During his show, Jack asks one audience member where he is from. When the man says he is from New Hampshire, which Jack mistakenly refers to as the "Windy City", the nickname for Chicago.
- Jack mentions that Will tried to get Michael back after breaking up by singing a medley of Peter, Paul, and Mary songs but "Michael rowed his boat ashore to another guy", referring to the Civil War song Michael Rowed His Boat Ashore which was covered by Peter, Paul, and Mary in 1998.
|Will:||You know the souvlaki vendor at the corner of 72nd and Central Park West? Really cute?|
|Jack:||Yeah. He is kind of... Gasp! No, you didn't?|
|Jack:||But he doesn't speak a word of English!|
|Jack:||That is so hot!|
We had this fantastic dinner at B.J., then we took one of those hansom cab rides around central park. It was so romantic, it didn't even bother me that the horse's tail kept hitting me in the mouth. — Grace
The guy didn't speak a word of English, but fortunately, Will's fluent in skank. — Jack