Kissing a Fool (1998)
R
93 min | Comedy, Romance

Kissing a Fool (1998)

93 min | Comedy, Romance

Writer Jay and womanizing sportscaster Max have been friends since birth. Jay introduces his editor Samantha to Max and they hit it off. Max wants Jay to try to seduce Sam to test her before their wedding.

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Cast	+ Add Cast
30 cast members

Name	Known for
David Schwimmer Max Abbitt Max Abbitt See fewer	Friends (1994)
Jason Lee Jay Murphy Jay Murphy See fewer	Almost Famous (2000)
Mili Avital Samantha Andrews Samantha Andrews See fewer	Stargate (1994)
Bonnie Hunt Linda Linda See fewer	Jumanji (1995)
Vanessa Angel Natasha Natasha See fewer	Kingpin (1996)
Kari Wuhrer Dara Dara See fewer	Eight Legged Freaks (2002)
Frank Medrano Cliff Randal Cliff Randal See fewer	The Shawshank Redemption (1994)
Bitty Schram Vicki Pelam Vicki Pelam See fewer	A League of Their Own (1992)
Judy Greer Andrea Andrea See fewer	13 Going on 30 (2004)
Ron Beattie Priest Priest See fewer	Miracle on 34th Street (1994)
Doug Ellin Bartender / Springer Guest Bartender / Springer Guest See fewer	Entourage (2004)
Tag Mendillo Wedding Guest at Bar / Springer Guest Wedding Guest at Bar / Springer Guest See fewer	Model Citizen (V)
Justine Bentley Beautiful Woman at Bar Beautiful Woman at Bar See fewer	The Ice Harvest (2005)
Liza Cruzat Dara's Friend #1 Dara's Friend #1 See fewer	I'm Gonna Git You Sucka (1988)
Jessica Mills Dara's Friend #2 Dara's Friend #2 See fewer	Kissing a Fool (1998)
Sammy Sosa Sammy Sosa Sammy Sosa See fewer	Hardball (2001)
Jerry Springer Jerry Springer Jerry Springer See fewer	Domino (2005)
Mike Squire Spanish Man in Bed Spanish Man in Bed See fewer	Blues Brothers 2000 (1998)
Marco Siviero French Man in Bed French Man in Bed See fewer	Keycards (2010)
Steve Seagren Heckler Heckler See fewer	Elizabethtown (2005)
Philip Rayburn Smith Fan on the Street (as Philip R. Smith) Fan on the Street (as Philip R. Smith) See fewer	Widows (2018)
Jayson Fate Rudolpho Rudolpho See fewer	Kissing a Fool (1998)
Ross Bon Blue Kings Lead Singer Blue Kings Lead Singer See fewer	Satin (2011)
Antimo Fiore Tony Tony See fewer	Stir of Echoes (1999)
Andy-John Dining Host (uncredited) Dining Host (uncredited) See fewer	Chicago Fire (2012)
Charles William Breen Jay's Agent (uncredited) Jay's Agent (uncredited) See fewer	Eight Legged Freaks (2002)
Christopher Free Springer Audience Member (uncredited) Springer Audience Member (uncredited) See fewer	Epitaph: Bread and Salt (2013)
Amy McLott Beautiful Woman on Rollerblades (uncredited) Beautiful Woman on Rollerblades (uncredited) See fewer	Judicial Consent (1995)
Sean Riggs Bar Patron (uncredited) Bar Patron (uncredited) See fewer	Lazarus (I) (2021)
Shannon Watson Timmy (uncredited) Timmy (uncredited) See fewer	The Sleeper (2007)

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