May 8th, 1999
Cuba Gooding, Jr.
Clinton’s DreamSummary: Bill Clinton (Darrell Hammond) imagines his post-presidential life with his second wife, Monica Lewinsky.
Recurring Characters: President Bill Clinton, Vernon Jordan, Betty Currie.
Note: During the live show, the dog runs off the set before President Clinton can pet him.
Cuba Goodinght, Jr.’s MonologueSummary: The audience waits on pins and needles for Cuba Gooding Jr. to say his signature catch phrase, “Show me the money!”
Improvised Bible MiniseriesSummary: In a bold creative move, a TV-movie director (Chris Parnell) asks his actors (Cuba Gooding Jr., Will Ferrell) to improvise the dialogue for a Bible-based miniseries.
Looking for Monica ISummary: Barbara Walters (Cheri Oteri) scours the halls of Studio 8-H in search of Monica Lewinsky.
Recurring Characters: Barbara Walters.
Pretty LivingRecurring Characters: Gayle Gleason, Helen Madden.
The Ladies ManSummary: Ladies Man Leon Phelps (Tim Meadows) welcomes Monica Lewinsky to the show.
Recurring Characters: Leon Phelps.
TV FunhouseSummary: Set in high school, “AmbiguoBoys” serves as prequel to the adventures of the Ambiguously Gay Duo.
Looking for Monica IIRecurring Characters: Barbara Walters.
Ricky Martin performs “Livin’ La Vida Loca”
Weekend Update with Colin QuinnRecurring Characters: Jesse Jackson.
Cuba Loves MangoSummary: Cuba Gooding, Jr.’s obsession with Mango (Chris Kattan) leads to the discovery that the flamboyant enigma has a wife (Molly Shannon) and family.
Recurring Characters: Mango.
Martha Stewart LivingRecurring Characters: Martha Stewart.
Looking for Monica IIIRecurring Characters: Barbara Walters.