Grace 0, Jack 2000 is the fifth episode of the third season and the 50th 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.