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These are the episodes airdates, their hosts, and what happened in the Ladies Man sketch in it.
Season 26
October 7, 2000 - Rob Lowe
Tim made a guest appearance on "Weekend Update" as Leon to promote sex in movies, his sexy movie: Ladies Man, and the Michael Richards Show.
Season 25
May 20, 2000 - Jackie Chan
Leon with Sarah Michelle Gellar, Gina Gershon, and Florence Henderson playing skanks in a rowdy game of "Who Wants to be My Skank?"
March 18, 2000 - The Rock
The Rock plays an undercover cop dressed as a woman who Leon hits on.
December 11, 1999 - Danny DeVito
A Ladies Man Christmas greeting complete with Leon singing.
October 16, 1999 - Heather Grahm
Leon chats about '70's porno films with Rollergirl.
Season 24
May 8, 1999 - Cuba Gooding Jr.
The actual Monica Lewinsky and John Goodman as Linda Tripp talk about phone sex.
February 20, 1999 - Bill Murray
How Leon Phelps goes on dates. "Leon, how about I introduce you to my parents." "I have a better idea, how about you pay the check and I climb out the bathroom window."
November 12, 1998 - Jennifer Love Hewitt
The Ladies Man Skanksgiving Special.
September 26, 1998 - Cameron Diaz
The Ladies Man Presents: Leon and skank re-enact the "Oral Office" and give some advice to the prez.
Season 23
May 2, 1998 - Mathew Broderick
The Ladies Man talks Viagra and "the fine Ms. Delta Burke."
March 14, 1998 - Julianne Moore
Leon has a guest skank (Julianne Moore) on the show. She's the skank that says that line from the commercials: "Come on down and I'll show you the finest rugs in town."
February 14, 1998 - Roma Downey
A Valentines edition of the Ladies Man.
December 13, 1997 - Helen Hunt
With help from Helen, Leon assures people like "Dinky Wang Man" that he will "never be able to pleasure a woman."
November 8, 1997 - Jon Lovitz
Leon and Tracy answer calls from old people and mention Delta Burke.
October 4, 1997 - Matthew Perry
The Ladies Man answers all your sexual and romantic queries.
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