List compiled by Eddie on 25/10/2018

For people of a younger age it may be hard to believe that there was a time when comedian Adam Sandler actually made funny movies.

Relegated these days to mostly lazy and uninspired so called comedies or Netflix tripe like The Ridiculous 6 or The Week Of, Sandler has had a quite spectacular fall from grace, yet while no one would be able to defend the immature nature of many of his film’s, there was a certain charm and enticing nature to Sandler’s work in the mid 90’s through to the mid 2000’s.

In amongst all of his slapstick comedies and juvenile adventures Sandler has also displayed an often untapped ability to actually act, that has shined forth in his more serious ventures like the recent Meyerowitz Stories and the underseen Reign Over Me and Punch Drunk Love, showcasing to all the naysayers that deep down there is a man of ability and intelligence hidden amongst the Grown Ups and Little Nicky’s.

In a career that has spanned over 30 years and 50 plus feature film’s, below is the best of what Adam Sandler has been able to conjure up.

Happy reading and happy watching.

10. Billy Madison (1995)

Sandler plays – Billy Madison

Sandler’s big break after a number of year’s in the comedy scene, Billy Madison is very far from quality cinema and hasn’t aged all that well, but at the time, this box-office hit was all the rage and a good example of Sandler’s unique ability to make dumb work.

Features Rob Schneider? – No

9. The Wedding Singer (1998)

Sandler plays – Robbie Hart

Teaming up for the first time with co-star Drew Barrymore, Sandler found a neat chemistry with the actress that made this tale of wedding singer Robbie Hart chasing the girl of his dreams a likeable and easy to enjoy rom-com.

Features Rob Schneider? – No

8. The Waterboy (1998)

Sandler plays – Bobby Boucher

Alongside The Wedding Singer, Sandler’s headlining appearance in the box-office smash The Waterboy ensured 1998 was quite the year for the comedian. Featuring absurd scenarios and scene-stealing turns from the likes of Henry Winkler, The Waterboy is the type of 90’s comedy they just don’t make these days.

Features Rob Schneider? – Yes

7. The Longest Yard (2005)

Sandler plays – Paul Crewe

Remaking the classic Burt Reynolds film, Sandler assembled an all-star comedic cast that included Chris Rock and Terry Crews and enough McDonald’s endorsements for a life time to bring this prison comedy to life and acting as another huge box-office hit for the actor, The Longest Yard was another bout of good dumb fun that just so happens to be a lot better with a character called Cheeseburger Eddie.

Features Rob Schneider? – Yes

6. The Meyerowitz Stories (New and Selected) (2017)

Sandler plays – Danny Meyerowitz

One of more memorable Netflix released film’s, The Meyerowitz Stories finds Sandler on more serious form and alongside his co-star Ben Stiller and famed director Noah Baumbach, Sandler creates one of his most memorable creations in the form of the middle aged Danny Meyerowitz. A funny and touching examination of a dysfunctional family, this is a prime example of Sandler’s ability to be more than he often showcases.

Features Rob Schneider? – No

5. Big Daddy (1999)

Sandler plays – Sonny Koufax

Filled with a healthy dose of Hollywood schmaltz and some misguided emotional sentiments, Big Daddy offered viewers a different look at Sandler who dialled it back a bit with this more seriously tinged comedy on parenthood and life. Big Daddy is the type of film you know you shouldn’t like but can’t help yourself from enjoying and remains one of the more readily accessible Sandler comedies to be released.

Features Rob Schneider? – Yes

4. 50 First Dates (2004)

Sandler plays – Henry Roth

Enlisting his Wedding Singer co-star Drew Barrymore for an excuse to holiday on the Hawaiian islands, Sandler struck it big at the box office once more with this randomly affecting rom-com that tackles the high-concept idea of dating someone with a very bad case of amnesia. Filled with good intentions and a beating heart, 50 First Dates remains one of better examples of modern rom-coms.

Features Rob Schneider? – Yes

3. Reign Over Me (2007)

Sandler plays – Charlie Fineman

Underseen and underrated upon release, Mike Bender’s touching September 11 themed drama was the first real chance we ever had at seeing Sandler stripped completely bare of his comedic hijinks and what a treat it was. Alongside his co-star Don Cheadle, Sandler created a forlorn and sad figure in the form of the grieving Charlie Fineman and helped make Reign Over Me a touching and emotionally resonate examination of life, love and loss.

Features Rob Schneider? – No

2. Punch Drunk Love (2002)

Sandler plays – Barry Egan

Teaming up with esteemed director Paul Thomas Anderson was one of the great moves of Sandler’s career and while Punch Drunk Love never broke out in a mainstream fashion, Punch Drunk Love remains the great director’s finest hidden gem. A bizarre head-trip of a film that is similar in fashion to Anderson’s more recent Inherent Vice, Punch is a film worth seeking out and further proof that Sandler would do well to seek out more untypical fair moving forward.

Features Rob Schneider? – No

1. Happy Gilmore (1996)

Sandler plays – Happy Gilmore

While it’d be hard to argue about the cinematic quality of this golfing themed comedy, there’d also be little point arguing against the fact that Happy Gilmore is one of the great examples of dumb comedy done right. The film that well and truly sent Sandler into the next level of Hollywood, Happy Gilmore remains a fond fan favourite and one of the most beloved comedies of the modern era.

Features Rob Schneider? – No

What are your favourite Sandler films? Do you prefer your Sandler funny or serious? Let me know in the comments below, I would love to hear from you!

For my other Actor Top 10’s see below –

Tom Hanks

Robert De Niro

Leonardo Di Caprio

Bruce Willis

Nicolas Cage

Russell Crowe

Denzel Washington

Brad Pitt

Tom Cruise

Johnny Depp

Clint Eastwood

Al Pacino

Jim Carrey

Mel Gibson

Christian Bale