Happy Madison Productions

Sandler formed his film production company, Happy Madison Productions,^[19] in 1999, first producing fellow SNL alumnus Rob Schneider's film Deuce Bigalow: Male Gigolo. Happy Madison has produced all of Sandler's subsequent films to date with the exceptions Punch-Drunk Love and Spanglish. Reign Over Me and Funny People were produced by Happy Madison but under the subsidiary label "Madison 23".

Sandler at a press conference for Click in 2005.

Sandler is known for consistently working with a core group of friends and associates through Happy Madison, frequently casting fellow SNL performers in various roles in his films. Sandler and Happy Madison produced SNL contemporary Rob Schneider's vehicles Deuce Bigalow: Male Gigolo (1999), The Animal (2001), The Hot Chick (2002), and Deuce Bigalow: European Gigolo (2005), and The Benchwarmers (2006), with Sandler making cameo appearances in the middle three. Meanwhile, Schneider has appeared in cameo roles in Sandler films The Waterboy, Little Nicky, Mr. Deeds, Click, The Longest Yard, I Now Pronounce You Chuck and Larry, and Bedtime Stories. Schneider had larger roles in Sandler films Big Daddy, 50 First Dates, Eight Crazy Nights, You Don't Mess with the Zohan, and Grown Ups.

Sandler's handprints and shoeprints in front of Grauman's Chinese Theatre, 2008.

Happy Madison produced David Spade's Joe Dirt, Dickie Roberts: Former Child Star, and The Benchwarmers, which also featured Rob Schneider.^[19] Spade additionally made a cameo appearance in I Now Pronounce You Chuck and Larry and had a prominent supporting role in Grown Ups. Sandler cameoed as a special audience member in an episode of The Showbiz Show with David Spade. SNL contemporary Kevin Nealon has appeared in ten Happy Madison productions or Sandler films, including Happy Gilmore, The Wedding Singer, Little Nicky, Joe Dirt, Eight Crazy Nights, Anger Management, Grandma's Boy, You Don't Mess with the Zohan, Just Go With It and the Dana Carvey vehicle, The Master of Disguise.

Happy Madison also produced Paul Blart: Mall Cop, the first starring vehicle for Kevin James. James had costarred with Sandler in I Now Pronounce You Chuck and Larry and Grown Ups and made a cameo appearance in You Don't Mess with the Zohan. Happy Madison also produced James' second starring vehicle Zookeeper.

He appeared as the featured guest on the final episode of John McEnroe's eponymous CNBC talk show, airing in late 2004. McEnroe appeared as himself in three of Sandler's films (Mr. Deeds, Anger Management, and You Don't Mess with the Zohan).

Anna Faris, who appeared in The Hot Chick, became the first female actor to headline a production for Happy Madison with The House Bunny and will headline another film for Happy Madison in the near future.

Others who frequently appear in Sandler films include Steve Buscemi, Chris Rock, John Turturro, Jon Lovitz, Clint Howard, Norm Macdonald, Nick Swardson, and longtime friends Allen Covert, Peter Dante, and Jonathan Loughran. Covert starred in his first leading role in Grandma's Boy, also produced by Happy Madison productions.

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