Meanwhile, Drew's brother Steve Carey (John Carroll Lynch) and his fiancée Mimi Bobeck (Kathy Kinney) hold a joint bachelor and bachelorette party.
To make "Drew Live" stand out, two-minute improvisational segments, in which the cast had to invent their own lines, were added in during filming.
It received mixed reviews from critics, with The Boston Globe's Matthew Gilbert calling it "gimmicky" and "a smug mess".
David Bianculli from the Daily News branded it "a hoot", and Bill Brioux of Canoe.ca praised the cast for being "fearless".
Steve becomes upset with his fiancée, Mimi (Kathy Kinney), when she reveals the plans for her bachelorette party include a visit to a strip club.
Kate O'Brien (Christa Miller) tells Lewis Kiniski (Ryan Stiles) that since Drew is dating again, she is finally going to confess her feelings for him.
At the party, Drew nervously waits for Kate, while Steve is worried about the men making the ladies feel uncomfortable with their bad behavior.
When Drew finally gets the chance to speak with Kate, he tells Oswald that he does not feel that he is ready to be in a serious relationship with her because he has behaved badly.
On July 28, 1999, Don Aucoin from The Boston Globe reported that The Drew Carey Show would film a live, partly unscripted episode in November that year.
[1] Executive producer and series co-creator, Bruce Helford commented "It's live, there's gonna be improv, anything can happen.
[6] Jamie Tarses, the head of ABC entertainment, stated that Helford and Carey had wanted the episode to be "live everywhere".
"[4] Security on the set was increased and the episode was broadcast with a small delay in case one of the actors said an offensive word.
[8] Similarly, Ryan Stiles was also a regular on Whose Line Is It Anyway?,[6] and he and Kathy Kinney had performed live improv for over 20 years.
[8] As Miller and Diedrich Bader were not improv comics and more likely to struggle, Stiles told Susan King from the Los Angeles Times that he was on "damage control" during filming.
[10] In its original broadcast, "Drew Live" was watched by 19.1 million viewers and finished 10th in the ratings for the week of November 8–14, 1999.
[5] He branded the episode "a hoot", and observed that Carey, Bader, Stiles, Sherwood and Mochrie handled the live element the best.
[5] The Boston Globe's Matthew Gilbert was not a fan of the episode, calling it "gimmicky", "a smug mess", and a "not-too-subtle" promotion for Whose Line Is It Anyway?
[15] Greg Hassall from The Sydney Morning Herald gave the episode a thumbs up and said it was "Little more than a blokey version of theatresports, the format suits the show's ramshackle, self-congratulatory style.