8. Billy Madison (1995)
When thinking of peak Adam Sandler, it’s hard to look beyond his performance in the utterly ridiculous yet somehow quite endearing Billy Madison (1995). The comedy actor, at the time just 29, burst onto the scene with his mid-90s work, Billy Madison being widely acknowledged as the beginning of Sandler’s box office draw as a lead star, and to this day it remains arguably his greatest comedic work.
In the movie he has all the juvenile delinquencies that so vastly appealed to Generation X, while the naivety he managed to attach to the character became one of his many comedic trademarks.
Billy Madison is hardly going to have people pointing at Sandler to win awards, but it was the location for one of the greatest comedy performances of his long career.
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7. Happy Gilmore (1996)
So, you know how we said Billy Madison was arguably the peak of Sandler’s comedy career? Well, consider it a close 2nd place…
Best remembered for the iconic physical encounter between Sandler’s titular character and the then sprightly 72 year old Bob Barker (TV’s nice guy – who was playing himself), this comedy took a lot of the principles of Billy Madison – including a lot of its predecessor’s narrative beats – and turned them up to 11 with the absurdist nature of the hockey player turned golfer concept, top notch celebrity cameos and many a memorable moment.
Sandler himself excelled in the utterly farcical concept, mixing authentic physical comedy moments with his now somewhat overplayed loud and expressionistic takes on lines.
6. Spanglish (2004)
Screenwriter-director James L. Brooks has a long history of subverting the expectations of his audiences by casting leading men in roles that counter their star personas. In 1997, Jack Nicholson was cast in Brooks’ Oscar-nominated rom-com As Good As It Gets, and in 2004 it was Adam Sandler’s turn to subvert expectations as the lead of family drama Spanglish.
Coming off the back of a critically acclaimed performance in the 2002 Paul Thomas Anderson movie Punch-Drunk Love, Sandler wasn’t exactly fresh to the dramatic fold, but his more serious work was still something we were all getting used to.
It seemed that through the guidance of Brooks, Sandler grew up, offering a more low-key performance in the somewhat serious albeit understated movie, bringing to the table something fresh and new even beyond that of his surprise success as a part of Punch-Drunk Love. Were it not for a run of average-to-bad comedies that followed this film, we could have been talking about this as the moment Sandler confirmed his dramatic credentials ahead of a lucrative dramatic career, but it wasn’t to be.