Home > Whose Line Is It Anyway? > Season 2 « TV Series Page Whose Line Is It Anyway?: Season 2 (1999 - 2000) SEASON: Season 2 Season 1 Season 2 Season 3 Season 4 Season 5 Season 6 Season 7 Season 8 Season 9 Season 10 Season 11 Season 12 Season 13 Season 14 Season 15 Episode List All Critics | Top Critics TOMATOMETER Tomatometer Not Available... —— Tomatometer Not Available... —— Critic Consensus: No consensus yet. AUDIENCE SCORE 87% liked it Average Rating: 4.4/5 User Ratings: 8 ADD YOUR RATING - NOT INTERESTED + WANT TO SEE Share on Facebook Post Want to See Not Interested Add Rating My Rating × Want to See Not Interested Post Share on Facebook Episodes 1 Air date: Sep 16, 1999 The second-season premiere includes Wayne Brady, Colin Mochrie and Ryan Stiles as singing lumberjacks-in-love; Brady impersonating "South Park" characters; Stiles as a hungry vulture; Drew Carey joining the others in a song about car salesmen; and Brady and Chip Estin warbling "Songs of the Dentist." Host: Drew Carey. More 2 (Episode 2) Air date: Sep 23, 1999 Colin Mochrie portrays a ship steward; Ryan Stiles jumps around like a hyperactive dog; Drew Carey joins in a bit about vice. Also: "Weird Newscasters." With Wayne Brady and Brad Sherwood. Host: Drew Carey. More 3 (Episode 3) Air date: Sep 30, 1999 Included: Greg Proops portrays a disagreeable co-anchor in a game of "Weird Newscasters"; Wayne Brady sings "Songs of the Exterminator"; host Drew Carey participates in a hoedown about The Village People. With Ryan Stiles and Colin Mochrie. Accompanied by musicians Laura Hall and Linda Taylor. More 4 (Episode 4) Air date: Oct 7, 1999 Included: "Let's Make a Date," featuring Greg Proops as an exorcist, Colin Mochrie as a hockey goon and Ryan Stiles as a club bouncer; "Three-Headed Broadway Star"; and "World's Worst." Host: Drew Carey. Laura Hall and Linda Taylor provide music. More 5 (Episode 5) Air date: Oct 7, 1999 Included: "Weird Newscasters," with Chip Esten as a Broadway star, Wayne Brady as a teenage Drew Carey fan and Ryan Stiles as a harried weather forecaster; a hoedown about men; and a quiz on "Godzilla." Host: Drew Carey. Laura Hall, Linda Taylor and Anna Wanselias provide music. More 6 (Episode 6) Air date: Oct 14, 1999 Colin Mochrie does a stint as an attention-starved anchor in "Weird Newscasters"; Wayne Brady serenades a man in uniform; host Drew Carey joins in a hoedown about gambling. More 7 (Episode 7) Air date: Oct 21, 1999 A game of "Let's Make a Date" features Brad Sherwood as a truck-pull announcer, Colin Mochrie as a beauty queen and Ryan Stiles as King Kong; "Superheroes"; golf's "Greatest Hits"; and a "90-Second Alphabet." With Wayne Brady. Host: Drew Carey. Musicians: Laura Hall and Linda Taylor. More 8 (Episode 8) Air date: Oct 28, 1999 Included: A game of "Let's Make a Date," with Wayne Brady as a schoolmarm, Colin Mochrie as a priggish model and Ryan Stiles as a pompous frat boy; Colin portrays a dentist in "Sound Effects"; and Wayne and Josie Lawrence perform a rock opera duet. Drew Carey is the host. Musicians: Laura Hall and Linda Taylor. More 9 (Episode 9) Air date: Nov 4, 1999 Included: "Scenes from a Hat"; "Weird Newscasters" with Ryan Stiles; Wayne Brady, Brad Sherwood and Ryan perform as a "Three-Headed Broadway Star"; Drew Carey joins a Christmas hoedown. With Colin Mochrie. Host: Drew Carey. Musicians: Laura Hall and Linda Taylor. More 10 (Episode 10) Air date: Nov 4, 1999 Included: A game of "Superheroes" with Colin Mochrie and Greg Proops; a serenading Wayne Brady; Drew Carey joins Wayne and Ryan Stiles for "Three-Headed Broadway Star." Host: Drew Carey. Musicians: Laura Hall and Linda Taylor. More Show More Episodes Tv Season Info Genre: Comedy Network: CW Premiere Date: Sep 16, 1999 Cast Drew Carey Ryan Stiles Colin Mochrie Wayne Brady Karen Maruyama Charles Esten Show More Cast Episodes 1 Air date: Sep 16, 1999 The second-season premiere includes Wayne Brady, Colin Mochrie and Ryan Stiles as singing lumberjacks-in-love; Brady impersonating "South Park" characters; Stiles as a hungry vulture; Drew Carey joining the others in a song about car salesmen; and Brady and Chip Estin warbling "Songs of the Dentist." Host: Drew Carey. More 2 (Episode 2) Air date: Sep 23, 1999 Colin Mochrie portrays a ship steward; Ryan Stiles jumps around like a hyperactive dog; Drew Carey joins in a bit about vice. Also: "Weird Newscasters." With Wayne Brady and Brad Sherwood. Host: Drew Carey. More 3 (Episode 3) Air date: Sep 30, 1999 Included: Greg Proops portrays a disagreeable co-anchor in a game of "Weird Newscasters"; Wayne Brady sings "Songs of the Exterminator"; host Drew Carey participates in a hoedown about The Village People. With Ryan Stiles and Colin Mochrie. Accompanied by musicians Laura Hall and Linda Taylor. More 4 (Episode 4) Air date: Oct 7, 1999 Included: "Let's Make a Date," featuring Greg Proops as an exorcist, Colin Mochrie as a hockey goon and Ryan Stiles as a club bouncer; "Three-Headed Broadway Star"; and "World's Worst." Host: Drew Carey. Laura Hall and Linda Taylor provide music. More 5 (Episode 5) Air date: Oct 7, 1999 Included: "Weird Newscasters," with Chip Esten as a Broadway star, Wayne Brady as a teenage Drew Carey fan and Ryan Stiles as a harried weather forecaster; a hoedown about men; and a quiz on "Godzilla." Host: Drew Carey. Laura Hall, Linda Taylor and Anna Wanselias provide music. More 6 (Episode 6) Air date: Oct 14, 1999 Colin Mochrie does a stint as an attention-starved anchor in "Weird Newscasters"; Wayne Brady serenades a man in uniform; host Drew Carey joins in a hoedown about gambling. More 7 (Episode 7) Air date: Oct 21, 1999 A game of "Let's Make a Date" features Brad Sherwood as a truck-pull announcer, Colin Mochrie as a beauty queen and Ryan Stiles as King Kong; "Superheroes"; golf's "Greatest Hits"; and a "90-Second Alphabet." With Wayne Brady. Host: Drew Carey. Musicians: Laura Hall and Linda Taylor. More 8 (Episode 8) Air date: Oct 28, 1999 Included: A game of "Let's Make a Date," with Wayne Brady as a schoolmarm, Colin Mochrie as a priggish model and Ryan Stiles as a pompous frat boy; Colin portrays a dentist in "Sound Effects"; and Wayne and Josie Lawrence perform a rock opera duet. Drew Carey is the host. Musicians: Laura Hall and Linda Taylor. More 9 (Episode 9) Air date: Nov 4, 1999 Included: "Scenes from a Hat"; "Weird Newscasters" with Ryan Stiles; Wayne Brady, Brad Sherwood and Ryan perform as a "Three-Headed Broadway Star"; Drew Carey joins a Christmas hoedown. With Colin Mochrie. Host: Drew Carey. Musicians: Laura Hall and Linda Taylor. More 10 (Episode 10) Air date: Nov 4, 1999 Included: A game of "Superheroes" with Colin Mochrie and Greg Proops; a serenading Wayne Brady; Drew Carey joins Wayne and Ryan Stiles for "Three-Headed Broadway Star." Host: Drew Carey. Musicians: Laura Hall and Linda Taylor. More Show More Episodes Critic Reviews for Whose Line Is It Anyway?: Season 2 There are no critic reviews yet for Season 2. Keep checking Rotten Tomatoes for updates! Audience Reviews for Whose Line Is It Anyway?: Season 2 There are no featured audience reviews yet. Click the link below to see what others say about Whose Line Is It Anyway?: Season 2! 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