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- Season 2, Episode 19
- IMDb rating: 7.7
- IMDb votes: 30
- Air date: Jan. 13, 2000

This episode featured frequent recurring guest Greg Proops—comedian and voice actor in “Bob the Builder” who has appeared on the show 70 times—alongside Colin Mochrie, Wayne Brady, and Ryan Stiles. This episode marked the return of “Questionable Impressions,” a game where performers only speak in questions and use a different impression every time they re-enter the scene. The cast members and Proops also played “Scenes from a Hat,” “Weird Newscasters,” and “Three-Headed Broadway Star,” and closed out the episode with a puberty-themed “hoedown” alongside host Drew Carey.

- Season 1, Episode 5
- IMDb rating: 7.8
- IMDb votes: 30
- Air date: July 30, 2013

Olympic synchronized swimmers Mary Killman and Mariya Koroleva and guest comedian Jeff Davis (who’s appeared on the show 40 times) joined Wayne Brady, Colin Mochrie, and Ryan Stiles in the first season of the revived show. The four comedians gave their take on an escape movie while playing “Hollywood Director” (shedding some clothes in the process) and acted out a skiing mishap in “Forward/Reverse.” Mochrie, Brady, and Davis performed an entire scene sideways, Koroleva and Killman acted as props for Stiles and Mochrie in “Living Scenery,” and danced along to Davis and Brady’s boy band-style “Duet.”

- Season 2, Episode 5
- IMDb rating: 7.8
- IMDb votes: 30
- Air date: Oct. 8, 1999

Comedian, country singer, and actor Charles “Chip” Esten, who played Deacon Claybourne in “Nashville,” joined the regular cast for this episode—one of more than 40 appearances on the show during both runs. During the episode, Mochrie and Stiles recreated a scene from “Gone With the Wind” in the audience-generated game “Whose Line?” and all four performers sang a “Hoedown.” They also played “Weird Newscasters,” “Duet,” “Scenes from a Hat,” and “Questions Only.”

- Season 2, Episode 18
- IMDb rating: 7.8
- IMDb votes: 32
- Air date: Jan. 6, 2000

Game show host Brad Sherwood was the second most-featured guest in the show’s history after Greg Proops, appearing in 69 episodes. In this episode, the crew teamed up to deal with a mosquito crisis in “Superheroes,” raised money for sitcom stars in a game of “Telethon,” and also played “Film, Theatre and TV Styles,” “Song Titles,” “Sound Effects,” and “Three-Headed Broadway Star.”

- Season 1, Episode 11
- IMDb rating: 7.8
- IMDb votes: 48
- Air date: Jan. 13, 1999

Highlights of this episode included recurring guest Greg Proops' Bill Clinton impression, as well as Wayne Brady singing about postal workers in "Greatest Hits." The cast also played "Dating Service Videos," and rounded out the episode with "Film, Theatre, and TV Styles," "Weird Newscasters," and "Helping Hands" with host Drew Carey.

- Season 1, Episode 4
- IMDb rating: 7.8
- IMDb votes: 61
- Air date: Aug. 26, 1998

Brad Sherwood joins the crew in rapping about meeting someone in a park. Later, Sherwood plays the host in a game of “Party Quirks,” and Colin Mochrie pretends to be a skier who can’t stop running into things. Other games in this episode included “Weird Newscasters,” “Duet,” “Animals” “Props,” “Moving People,” and “Foreign Film Dub.”

- Season 2, Episode 4
- IMDb rating: 7.9
- IMDb votes: 32
- Air date: Oct. 7, 1999

In this episode, Wayne Brady chose between Greg Proops’ exorcist, Ryan Stiles’ club bouncer, and Colin Mochie’s fanatic Canadian hockey player during “Let’s Make a Date.” Other games featured in the episode included “Film Dub,” “Three-Headed Broadway Star,” “Film, Theatre, and TV Styles,” “Greatest Hits,” and “World's Worst.”

- Season 2, Episode 13
- IMDb rating: 7.9
- IMDb votes: 33
- Air date: June 16, 2014

Misha Collins took a break from fighting evil on the CW’s “Supernatural” to join the second season of the “Whose Line” revival. He became the subject of a “Duet” by Wayne Brady and recurring guest Brad Sherwood (in Russian folk style) and pretended to be “Living Scenery” for two friends’ motorcycle trip to Las Vegas. Sherwood acted as the fourth man in the rest of the episode’s games, “Let's Make a Date,” and “Scenes from a Hat,” and finished off the episode with a cheese-themed “Hoedown.”

- Season 2, Episode 3
- IMDb rating: 7.9
- IMDb votes: 33
- Air date: Sep. 30, 1999

As the episode’s winner, veteran guest Greg Proops looked on with delight as Drew Carey joined the cast in a “Hoedown” about the Village People (known for their hit “YMCA”). The cast also played “Weird Newscasters,” “African Chant,” “Scenes from a Hat,” “Change Emotion,” and a round of “Greatest Hits” featuring an exterminator.

- Season 2, Episode 1
- IMDb rating: 7.9
- IMDb votes: 38
- Air date: Sep. 16, 1999

The second season of the original American series opened with Wayne Brady officially joining the regular cast. Featuring frequent guest performer Chip Esten as the episode's fourth participant, the cast performed a song about lumberjacks in love during "Three-Headed Broadway Star," and played "Let's Make a Date," "Props," "Stand Sit Lie Down," "Greatest Hits," and "Hoedown."

- Season 1, Episode 6
- IMDb rating: 7.9
- IMDb votes: 64
- Air date: Sep. 9, 1998

Aired before Wayne Brady joined the regular cast, this episode featured guest performers Brad Sherwood and actress Kathy Kinney, (“The Drew Carey Show” and “Newhart”) in her first and only appearance on the show. Kinney played the distressed mother of the “three little pigs” during a game of “Daytime Talk Show” in one of the episode’s stand-out moments. The cast also played “Let's Make a Date,” “Sound Effects,” “Props,” “Helping Hands,” “Hoedown,” and “90-Second Alphabet.”

- Season 2, Episode 29
- IMDb rating: 8.0
- IMDb votes: 30
- Air date: March 23, 2000

Colin Mochrie and Ryan Stiles played two secret agents on an “Improbable Mission” to do laundry for a visiting dignitary. Mochrie’s repeated use of “the cat!” to solve the mission’s problems has long made it one of the show’s most enduring sketches. Greg Proops contributed to “Let's Make A Date,” “Song Styles,” “Party Quirks,” and “Three-Headed Broadway Star.”

- Season 2, Episode 14
- IMDb rating: 8.0
- IMDb votes: 31
- Air date: Nov. 25, 1999

This episode marked the debut of “The Millionaire Show,” a parody of “Who Wants to Be a Millionaire?” In another highlight, the audience participated in a song about toothbrushes created by Stiles, Wayne Brady, and guest comedian Brad Sherwood. The cast also played “Superheroes,” “Film, Theatre and TV Styles,” “Props,” “Motown,” and finished up with a “Hoedown” about family reunions.

- Season 1, Episode 14
- IMDb rating: 8.0
- IMDb votes: 46
- Air date: Feb. 3, 1999

Ian Gomez—known for his roles on the “Drew Carey Show,” “Felicity,” and “Cougar Town”—joined regular guest Brad Sherwood for one of his two appearances on “Whose Line is it Anyway?” Gomez played a hybrid sportscaster/fed-up Ricky Ricardo during a “Weird Newscasters” segment. Other games featured in this episode were “Let's Make A Date,” “Moving People,” “Greatest Hits,” “Party Quirks,” and “Helping Hands.”

- Season 1, Episode 12
- IMDb rating: 8.0
- IMDb votes: 50
- Air date: Jan. 20, 1999

Wayne Brady and Brad Sherwood took to the stage to participate in a game of "Telethon" to benefit NBA players. A game of "Film, Theatre, and TV Styles" was another highlight: Brady and Stiles recreated the biopic "Birdman of Alcatraz" in the styles of Shakespeare, sumo wrestling, and adult film. The cast also played "Let's Make A Date," "Duet," "Newsflash," and "Hoedown."

- Season 1, Episode 1
- IMDb rating: 8.0
- IMDb votes: 102
- Air date: Aug. 5, 1998

The American version of “Whose Line is it Anyway?” kicked off with the show’s most frequent guest, Greg Proops, guessing his castmates’ strange “Party Quirks.” The episode started off with Ryan Stiles infamously portraying the birth of a foal. The rest of the episode—which included “Let's Make a Date,” “Sound Effects,” “Hats,” “Greatest Hits,” and “Foreign Film Dub”—wasn’t quite as bizarre, but still managed to start the series with a bang.

- Season 2, Episode 2
- IMDb rating: 8.1
- IMDb votes: 34
- Air date: Sep. 23, 1999

Recurring guest Brad Sherwood joined Drew Carey, Ryan Stiles, and Colin Mochie to serenade Wayne Brady (the episode’s “winner”) with a “Hoedown” about drinking too much. The performers also worked their way through “Weird Newscasters,” “Duet,” “Newsflash,” “Party Quirks,” and “Scenes from a Hat.”

- Season 1, Episode 3
- IMDb rating: 8.1
- IMDb votes: 46
- Air date: July 23, 2013

Candice King, best-known for her role as Caroline Forbes on the supernatural drama “The Vampire Diaries” and its spinoff “The Originals,” was featured in this episode. King was the subject of a Latin pop song by Wayne Brady during “Song Styles” and joined “Living Scenery” alongside two mountaineers climbing Mount Everest. This episode also marked the first appearance of actor and comedian Keegan-Michael Key, of “Key & Peele” and “MAD TV,” who has appeared on the show nine times. Key contributed to the rest of the episode’s games: “Hollywood Director,” “Props,” and “Dating Profiles.”

- Season 1, Episode 8
- IMDb rating: 8.1
- IMDb votes: 55
- Air date: Dec. 9, 1998

Denny Siegel, a correspondent on “The Daily Show,” made her first of 14 “Whose Line” appearances in this episode. Siegel took on the role of host in “Party Quirks” and a bachelorette in search of a partner on “Let’s Make a Date.” “Props,” a game of “Song Styles” about swimming lessons, the “Greatest Hits” of butchers everywhere, and “Helping Hands” rounded out the episode.

- Season 1, Episode 10
- IMDb rating: 8.1
- IMDb votes: 57
- Air date: Jan. 6, 1999

Denny Siegel returned for her second guest appearance to open the show with a melodramatic teen soap opera in "Questions Only." Wayne Brady's gospel-style song about an immigration attorney in "Song Styles" marked another highlight in this episode. The four comedians also played "Newsflash," "Sound Effects," "Weird Newscasters," "Scene to Rap," and "Hoedown."

- Season 2, Episode 10
- IMDb rating: 8.2
- IMDb votes: 30
- Air date: Nov. 5, 1999

Drew Carey joined Wayne Brady and Ryan Stiles in “Three-Headed Broadway Star” for the very first time, accidentally singing an entire line instead of just one word during “You’ve Got Sole” from made-up Broadway musical “My Favorite Shoe.” Other highlights included Greg Proops teaming up with the regular cast as “Superheroes” who have run out of deodorant, and Wayne Brady impersonating an aging Michael Jackson in “Song Styles.” The cast also played “Newsflash,” “Questionable Impressions,” and “Dating Service Video.”

- Season 2, Episode 22
- IMDb rating: 8.2
- IMDb votes: 31
- Air date: Feb. 4, 2000

In this episode, Colin Mochrie and Ryan Stiles acted out a film noir scene in a fast food restaurant during a game of “Narrate.” The scene famously ended with the two longtime collaborators kissing on-screen. Canadian actress and frequent series guest Kathy Greenwood played a woman dining with a colleague in a war zone during “Themed Restaurant,” and portrayed a bratty granddaughter in “Weird Newscasters.” The episode finished up with a racy singing telegram in “Song Styles,” after the cast played “Scenes From A Hat,” and sang a Halloween-themed “Hoedown.”

- Season 1, Episode 6
- IMDb rating: 8.2
- IMDb votes: 38
- Air date: Aug. 6, 2013

Actor Wilson Bethel, from the CW’s “Hart of Dixie” and Netflix's “Daredevil” appeared on this episode of “Whose Line is it Anyway?” Bethel was serenaded with a Motown-style “Duet” by Wayne Brady and frequent show guest Gary Anthony Williams, an actor and comedian known for roles in “Boston Legal” and “Harold and Kumar Go to White Castle.” Bethel also joined in for the three-headed song "I Can't Live Without Your Rubber Ducky.” Other games featured in the episode are “Helping Hands,” “Sideways Scenes,” and “Weird Newscasters.”

- Season 1, Episode 2
- IMDb rating: 8.2
- IMDb votes: 49
- Air date: July 16, 2013

“Whose Line is it Anyway” launched its first season after a six-year hiatus by bringing on several new celebrity guests, including Kevin McHale of hit TV show “Glee.” Former “Saturday Night Live” writer Heather Anne Campbell also contributed to games of “Scenes from a Hat,” “Song Styles,” “Dubbing,” “Sideways Scene,” and “Helping Hands.”

- Season 1, Episode 1
- IMDb rating: 8.2
- IMDb votes: 64
- Air date: July 16, 2013

Lauren Cohan, from FX's "The Walking Dead," was the inaugural guest on the revival of "Whose Line is it Anyway?" acting out a zombie apocalypse in "Dubbing" and playing a prop in "Living Scenery." Actor and comedian Gary Anthony Williams also made his "Whose Line" debut on the new version of the show, participating in "Let's Make a Date," "Dubbing," "What's in the Bag," and "Scenes from a Hat." He's since appeared in 22 episodes.

- Season 2, Episode 39
- IMDb rating: 8.3
- IMDb votes: 31
- Air date: May 18, 2000

Chip Esten and Wayne Brady teamed up for “Duet,” serenading a sandwich shop employee. Drew Carey joined in for “Foreign Film Dub,” translating a film into “Canadian.” In one of the show’s best-known “Newsflash” segments, Colin Mochrie reported in front of a green screen flashing pictures of himself, and kicked off the segment by claiming that "it all started with a badly timed bald joke,” without realizing the context. “Song Titles” and a “Hoedown” about plastic surgery rounded out this episode.

- Season 8, Episode 16
- IMDb rating: 8.4
- IMDb votes: 31
- Air date: Nov. 10, 2006

Greg Proops joined this episode, playing a game of “Superheroes” in which the four performers formed an odd band of heroes facing off against a global beer crisis. The episode also featured “Sound Effects,” “Props,” “Hey You Down There,” “Daytime Talk Show,” “Scene to Rap,” and “Hats.”

- Season 3, Episode 0
- IMDb rating: 8.8
- IMDb votes: 32
- Air date: Oct. 4, 2000

This clip show that aired just before the show’s third season featured host Drew Carey introducing some of the first two seasons’ most memorable moments. It also presented a number of bloopers and outtakes from the show that didn’t make it to air.

- Season 3, Episode 9
- IMDb rating: 8.8
- IMDb votes: 66
- Air date: Nov. 16, 2000

Robin Williams’ sole appearance on “Whose Line is it Anyway” gave the comic legend a chance to show off . He for “Film Director” (featuring "Riverdance"), sang gospel during “Duet,” played a fashion-conscious party guest during “Party Quirks,” and participated in “Scenes From A Hat” and “Props.”

- Season 5, Episode 17
- IMDb rating: 9.2
- IMDb votes: 76
- Air date: June 20, 2003

Regular guest performer Greg Proops (who appeared in 70 episodes) joined the cast for "Multiple Personalities" and "Newsflash," both of which featured jokes about flamboyant celebrity fitness personality Richard Simmons. Simmons himself later surprised the cast and audience to great effect, participating in "Song Styles," "Living Scenery," and "Moving People." Simmons' appearance in "Living Scenery" is considered one of the most infamous scenes in the entire series, due to his exaggerated signature racy gestures.