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The Best Episodes of Whose Line Is It Anyway? Season 5

Every episode of Whose Line Is It Anyway? Season 5 ranked from best to worst. Discover the Best Episodes of Whose Line Is It Anyway? Season 5!

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The show where everything's made up and the points don't matter. Not a talk show, not a sitcom, not a game show, Whose Line Is It Anyway? is a completely unique concept to network television.

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Episode Rankings

  1. #1 Fan Favorite
    Whose Line Is It Anyway? Season 5 Episode 17 - Greg Proops
    9.4/10(191 votes)

    S5:E17

    Exercise maven---and frequent punchline--- Richard Simmons joins the guys for a round of “Living Props” and sweats to the ditties during a disco-themed “Song Styles.” Also: “Multiple Personalities” and “Newsflash.”

    Director:Unknown
    Writer:Unknown

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  2. Whose Line Is It Anyway? Season 5 Episode 4 - Brad Sherwood
    8.3/10(68 votes)

    S5:E4

    Florence Henderson drops by for a round of “Duet” and a game in which words containing the letter L are forbidden. Featuring Ryan Stiles, Colin Mochrie and Wayne Brady. Drew Carey is the host.

    Director:Unknown
    Writer:Unknown

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  3. Whose Line Is It Anyway? Season 5 Episode 18 - Brad Sherwood
    8.3/10(51 votes)

    S5:E18

    Games include “Press Conference,” featuring Colin Mochrie as Batman; and a round of “All in One Voice,” which finds the guys channeling a piggy puppet to serenade one another. Wayne Brady, Ryan Stiles and host Drew Carey also perform.

    Director:Unknown
    Writer:Unknown

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  4. Whose Line Is It Anyway? Season 5 Episode 20 - Greg Proops
    8.3/10(61 votes)

    S5:E20

    Greg Proops tries to get his groove on in a round of “Weird Newscasters.” Also: “Scenes from a Hat”; “Film Dub”; “Party Quirks”; and “World's Worst Dating Service Video.” Other players include Colin Mochrie and Ryan Stiles.

    Director:Unknown
    Writer:Unknown

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  5. Whose Line Is It Anyway? Season 5 Episode 1 - Whoopi Goldberg
    8.2/10(67 votes)

    S5:E1

    Whoopi Goldberg drops in for some improv games. Cast regulars include Ryan Stiles, Colin Mochrie, Wayne Brady and host Drew Carey.

    Director:Unknown
    Writer:Unknown

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  6. Whose Line Is It Anyway? Season 5 Episode 3 - Brad Sherwood
    8.2/10(55 votes)

    S5:E3

    Games include a round of “Props” with host Drew Carey; and “Awards,” with Brad Sherwood and Wayne Brady as presenters at a function honoring frat boys. Also: “Scenes from a Hat.” Ryan Stiles and Colin Mochrie also appear.

    Director:Unknown
    Writer:Unknown

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  7. Whose Line Is It Anyway? Season 5 Episode 19 - Kathy Griffin
    8.2/10(46 votes)

    S5:E19

    David Hasselhoff drops by for a round of “Song Styles” with Wayne; and a game called “Dubbing,” in which he plays (what else?) a lifeguard. Also: “News Flash” and “Two-Line Vocabulary.” Other players include Ryan Stiles, Colin Mochrie and host Drew Carey.

    Director:Unknown
    Writer:Unknown

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  8. Whose Line Is It Anyway? Season 5 Episode 11 - Brad Sherwood
    8.1/10(60 votes)

    S5:E11

    Skits include a party with a diverse guest list (a safari guide and a nudist among them), and a scandal-plagued wedding. Also: host Drew Carey sings about marriage. Performers include Ryan Stiles, Colin Mochrie, Wayne Brady and Brad Sherwood.

    Director:Unknown
    Writer:Unknown

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  9. Whose Line Is It Anyway? Season 5 Episode 15 - Kathy Griffin
    8.1/10(41 votes)

    S5:E15

    Guest Kathy Griffin plays a teenage groupie. Also: Wayne Brady as Don King promoting an “improve your sex life” video; Ryan Stiles as a David Copperfield wannabe.

    Director:Unknown
    Writer:Unknown

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  10. Whose Line Is It Anyway? Season 5 Episode 32 - Jeff Davis
    8.1/10(53 votes)

    S5:E32

    Instead of points, the players win $100 for winning rounds, which include a pair of pop divas duking it out during “Weird Newscasters”; “Scenes from a Hat”; and “Greatest Hits.”

    Director:Unknown
    Writer:Unknown

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  11. Whose Line Is It Anyway? Season 5 Episode 8 - Brad Sherwood
    8.0/10(41 votes)

    S5:E8

    Former WWF wrestler Joanie Laurer (“Chynna”) takes on the gang in a round of improv games.

    Director:Unknown
    Writer:Unknown

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  12. Whose Line Is It Anyway? Season 5 Episode 14 - Chip Esten
    8.0/10(54 votes)

    S5:E14

    Games include Wayne as a whole family of acrobats in “Let's Make a Date”; and Ryan as the star of “Drew Carey, The Musical.” Also: A round of “Dubbing”; “Scenes From a Hat”; and “Props.” Other players include Colin Mochrie and host Drew Carey.

    Director:Unknown
    Writer:Unknown

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  13. Whose Line Is It Anyway? Season 5 Episode 16 - Brad Sherwood
    8.0/10(56 votes)

    S5:E16

    Wayne Brady loses more than his shirt at a casino, and plays both Michael Jackson and James Brown in a “celebrity death match.” Also: the Blues Brothers sing to a sign-language interpreter; and host Drew Carey joins in a “Hoedown” about growing up.

    Director:Unknown
    Writer:Unknown

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  14. Whose Line Is It Anyway? Season 5 Episode 10 - Greg Proops
    7.9/10(43 votes)

    S5:E10

    Games find Greg Proops looking for love in “Let's Make a Date”; Wayne Brady riffing on Tom Cruise movies in “Scene to Rap”; and host Drew Carey playing the “World's Worst” psychiatrist. Also: “Scenes from a Hat.” Ryan Stiles and Colin Mochrie also play.

    Director:Unknown
    Writer:Unknown

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  15. Whose Line Is It Anyway? Season 5 Episode 21 - Greg Proops
    7.9/10(57 votes)

    S5:E21

    Colin and Ryan play sorority girls with unusual athletic abilities in “Sportscasters”; Colin goes psycho as an unstable flight attendant in “Let's Make a Date”; Wayne croons to a female bodybuilder in “Song Styles.”

    Director:Unknown
    Writer:Unknown

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  16. Whose Line Is It Anyway? Season 5 Episode 23 - Kathy Greenwood
    7.9/10(39 votes)

    S5:E23

    In a round called “Number of Words,” the players can only speak so many lines of dialogue, all from ”The Wizard of Oz.” Players include Wayne Brady, Colin Mochrie and Ryan Stiles.

    Director:Unknown
    Writer:Unknown

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  17. Whose Line Is It Anyway? Season 5 Episode 31 - Brad Sherwood
    7.9/10(48 votes)

    S5:E31

    Games include “Hollywood Director,” with Ryan Stiles and Wayne Brady as Arctic explorers; and a round of “Two-Line Vocabulary” set in the wild, wild west. Also: Colin Mochrie tries to figure out who he is in “Press Conference.”

    Director:Unknown
    Writer:Unknown

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  18. Whose Line Is It Anyway? Season 5 Episode 34 - Chip Esten
    7.9/10(53 votes)

    S5:E34

    In "Hollywood Director," town sheriff Ryan has finally caught the fugitive gunslinger Chip and puts him in jail, but Wayne comes in as a member of Chip's gang, and Colin gives them the styles of falling in love with each other and product testimonials. In "Improbable Mission," Wayne is the voice on the tape informing secret agents Colin and Ryan that they must go shopping at the grocery store. In "Scenes From A Hat," the scenes are "bad times to use the athletic butt slap," "topics of conversation that always ruin dinner parties," "what the Whose Line? cast will ask Santa for this Christmas," and "things your waitress can say that can be misconstrued as sexual." In "Greatest Hits," Colin and Ryan sell Songs of Pregnancy, with songs performed by Wayne and Chip. Chip wins, so the rest join Drew for a game of "Props."

    Director:Unknown
    Writer:Unknown

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  19. Whose Line Is It Anyway? Season 5 Episode 5 - Greg Proops
    7.8/10(55 votes)

    S5:E5

    Games include “Scenes from a Hat,” “Song Styles,” “Multiple Personalities” and “Props.” Regulars include Ryan Stiles, Colin Mochrie and Wayne Brady.

    Director:Unknown
    Writer:Unknown

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  20. Whose Line Is It Anyway? Season 5 Episode 6 - Kathy Greenwood
    7.8/10(59 votes)

    S5:E6

    Games include a round of “Questions Only” dedicated to queries about “The Wizard of Oz”; “News Flash”; “Song Styles”; and a sexed-up “Sesame Street”-inspired rendition of “Scenes from a Hat.” Ryan Stiles, Colin Mochrie, Wayne Brady and Drew Carey.

    Director:Unknown
    Writer:Unknown

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  21. Whose Line Is It Anyway? Season 5 Episode 9 - Chip Esten
    7.8/10(55 votes)

    S5:E9

    In "Superheroes," Stinky Man (Colin) tries to solve a dead possum in his parking spot with his friends Giggling Nipple-Tweak Man (Ryan), Captain Luau (Chip), and Temper Tantrum Kid (Wayne); "Scenes from a Hat" are "disturbing people to get a lap dance from," "unfortunate times to sneeze," "jobs where you shouldn't kid around," and "the Munchkins: What are they doing now?"; "Stand, Sit, Lie" comes back after a three-season hiatus, with expectant mother Ryan is cared for by flirtatious midwife Wayne, with Colin the nervous husband; in "Party Quirks," Chip tries to guess various acts getting booed off the stage during Amateur Night at the Apollo (Wayne), a bomb squad member who received a tip that there are bombs in people's pants (Colin), and a series of ugly sea creatures swimming up to the cameras (Ryan); after finding humor in Drew nearly choking himself with a breath mint, the show continues with "Show-Stopping Number," featuring Ryan, Colin, and Wayne in a factory.

    Director:Unknown
    Writer:Unknown

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  22. Whose Line Is It Anyway? Season 5 Episode 26 - Jeff Davis
    7.8/10(55 votes)

    S5:E26

    Games include “Let's Make a Date”; “Hoedown”; “Scenes From a Hat”; and “News Flash.” Also: a round of “Greatest Hits.” The ensemble features Wayne Brady, Colin Mochire, Ryan Stiles and host Drew Carey.

    Director:Unknown
    Writer:Unknown

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  23. Whose Line Is It Anyway? Season 5 Episode 27 - Brad Sherwood
    7.8/10(50 votes)

    S5:E27

    Highlights include: Game 1 - Hollywood Director Colin, as usual, is the director Ryan and Wayne, two gold miners Brad, the bandito who has come to rob them. Directions from Colin: do the scene backwards do the scene full of lust for each other include as many "Your momma!" jokes as possible. Game 2 - If You Know What I Mean Brad and Colin are customers at a diner where Ryan is their waitress Penultimate game - Greatest Hits Songs Of Weddings including the B-52's singing Cash Bar. Artificial Winner - Wayne Drew Game - Helping Hands Drew is a high school student being taught lessons in French culture by Ryan, with the helping hands of Colin. Credits Roll - Wayne and Colin are trained seals being fed by Brad and Ryan.

    Director:Unknown
    Writer:Unknown

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  24. Whose Line Is It Anyway? Season 5 Episode 30 - Greg Proops
    7.8/10(55 votes)

    S5:E30

    Highlight include: Make A Monster Dubbing Scenes From A Hat Greatest Hits: Songs of Sci-Fi Aritificial Winner - Wayne Brady Drew Game - World's Worst: Things to say or do on your 1st day in prison Credits Roll - Greg reads the credits as a dancing monkey.

    Director:Unknown
    Writer:Unknown

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  25. Whose Line Is It Anyway? Season 5 Episode 33 - Greg Proops
    7.8/10(48 votes)

    S5:E33

    A round of “Hats” has the gang seeking clients for the world's worst dating service; audience members wind up playing “Let's Make a Date.”

    Director:Unknown
    Writer:Unknown

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Season 5 Ratings Summary

"Greg Proops" is the best rated episode of "Whose Line Is It Anyway?" season 5. It scored 9.4/10 based on 191 votes. Directed by Unknown and written by Unknown, it aired on 6/20/2003. This episode is rated 1.1 points higher than the second-best, "Brad Sherwood".