1. The Longest Yard
   Airheads
2. Going Overboard
   Happy Gilmore

Released in winter of 1996, Happy Gilmore pulled in an impressive $41.2 million at the worldwide box office on a $12 million dollar budget. The film also starred Christopher McDonald, Julie Bowen, Frances Bay, and Carl Weathers.

1. That's My Boy
   The Waterboy
2. The Longest Yard
   Billy Madison

Released in the fall of 1998, 'The Waterboy' tells a hilarious story of stuttering 31-year-old water boy named Bobby Boucher (Adam Sandler) who joins the Louisiana State University football team, against his overprotective mother's wishes.

1. That's My Boy
   Eight Crazy Nights
2. Billy Madison
   Blended

Adam Sandler was nominated for Best Comedic Performance at the 1995 MTV Movie Awards for his performance in Billy Madison. Despite some rather negative reviews from critics, the hilarious comedy pulled in roughly $26 million and debuted at number one at the box office.

1. Diver Dan
   Fresh Water Freddy
2. Swimmer Sam
   Scuba Steve

Scuba Steve

1. Click
   Just Go with It
2. Bedtime Stories
   The Cobbler

'Click' also stars Kate Beckinsale, Christopher Walken, Henry Winkler, Jennifer Coolidge, and Sean Astin. The 2006 science fantasy comedy grossed $237.7 million worldwide, and was nominated for the Academy Award for Best Makeup.

1. 50 First Dates
   Punch-Drunk Love
2. Bedtime Stories
   Reign Over Me

Back in 2004, Adam Sandler and Drew Barrymore won an MTV award for Best On-Screen Team for their portrays of Henry Roth and Lucy Whitmore. The romantic comedy has inspired various remakes overseas, including Malayalam movie called 'Ormayundo Ee Mukham.'

1. Sandy Wexler
   You Don't Mess with the Zohan
2. The Longest Yard
   The Ridiculous 6

Interestingly enough, 'The Longest Yard' is actually a remake of the 1974 film of the same name, starring Burt Reynolds. Which is why it was cool that the late actor was cast in the remake, this time around playing coach Nate Scarborough.

1. Eight Crazy Nights
   Grown Ups
2. The Do-Over
   The Week Of

Grown Ups was released in 2010 and stars Adam Sandler, Kevin James, Chris Rock, David Spade, and Rob Schneider. The comedy was not particularly well received by critics, but the movie still managed to gross an impressive $271.4 million.

1. Dave Buznik
   Robbie Hart
2. Charlie Fineman
   Lenny Feder

Adam Sandler and Drew Barrymore have co-starred as romantic partners in three movies over the years. The Wedding Singer was the first, followed by 50 First Dates in 2004 and Blended in 2014. The romantic comedy was a box office success, earning $123.3 million on a budget of only $18 million.

1. Drew Barrymore
   Jennifer Aniston
2. Courteney Cox
   Keri Russell

'Bedtime Stories' is about a hotel maintenance man named Skeeter Bronson (Adam Sandler) whose life is turned upside after he discover that the nighttime stories he has been telling his niece and nephew are actually coming true.