Granted, his filmography is a list of hits and misses, including The Bad News Bears Go to Japan (although I give him props for playing a caricature of himself on a Flintstones episode in 1965). That being said, there are two films that are easily his best work and are two of the funniest films ever.
The first is Operation Petticoat, a war comedy about a US sub commander (played by Cary Grant) in WWII who has to deal with a new recruit (Curtis) and his less-than-legal ways of getting things done. Grant was so suave in so many movies, it is great fun to see him stiff with Curtis ruffling his feathers. It’s a great, silly film and just a little bit raunchy (at least for the time).
The second is Some Like it Hot, arguably one of the greatest comedies of all time. With Jack Lemmon (another amazing comedic actor), Curtis played a jazz musician running from the mob who is forced to join a women’s big band by pretending to be a woman. It’s over-the-top and silly, but it’s so much fun. His character also ends up seducing Marylin Monroe’s character by hilariously portraying a meek millionaire; ironically, he parodied Cary Grant’s distinctive accent for the part. It is another great film and has one of the funniest and most memorable ending moments in all of film (if you don’t know what it is, go rent the movie. I refuse to ruin it for you).
Just by these two movies alone, Tony Curtis made his mark on cinema. Just in the last couple days, other movie buffs have praised some of his other films. Apparently, The Sweet Smell of Success is another great work. In any case, rest in peace, Mr. Curtis.