You know you’ve made it in the film business when your movies can be watched twenty years after you initially starred in them and they still hold up. Audiences and movie goers still think they’re funny, interesting and or great to watch.

Case in point? Billy Crystal. The comedic actor and former SNL alum is hosting this years Academy Awards show and aside from being an excellent host, he’s a terrific comedic actor in his own right and below we showcase five of his best most funnies films in his career.

5. Running Scared

This was my first introduction to Billy Crystal on the big screen and he didn’t disappoint. This was a buddy cop movie that starred Billy and tap dancing man Gregory Hines that also showcased Chicago in all its blue police car glory. Running Scared is funny, clever and was a huge hit way back in 1986 when Billy was just getting started in films. A must see if you’re a fan of good buddy cop movies.

running scared movie

4. Throw Momma From The Train

This was perhaps Billy Crystal’s most successful film in the late 80’s. It also stars Danny Devito and one very ornery Momma, actress Anne Ramsey. The film was dark and some complained a bit too dark on the humor, but it was a smash hit and audiences showed up in droves to see it. Throw Momma from The Train is classic Billy Crystal at his comedic best. If you like your humor a tad on the dark side, this is the movie for you.

throw momma from the train movie

3. Analyze This

Enter the 90’s and this brings us to Analyze This, a wildly successful film that also co-starred Robert De Niro as a thug needing therapy from the one and only Billy who in the movie plays a therapist. The film was a massive success garnering over $176 million at the box office.

analyza this movie

2. City Slickers

When you think of Billy Crystal this is probably one of the films that comes to mind as it garnered quite the following, not too mention it brought about a new resurgent popularity in western dude ranch vacations all over the US. City Slickers is about a group of friends who decide to go on a once in a lifetime vacation but not your garden variety vacation, an adventure packed dude ranch where one gets to ride horses, rope cattle and chase after other Wild Wild Wild West frontiers.

city slickers the movie

1. When Harry Met Sally

This movie came out in 1989 and it still holds up. The story revolves around a classic question – can men and women that like each other, be just friends? It goes on to try and answer this question via hilarious skits and great comedic lines including a few now infamous ones.

when harry met sally movie

Billy Crystal has cemented his place in Hollywood and in romantic comedies with not one, not two, not three – but several great roles in the films mentioned above. If you’re feeling a tad nostalgic this week, anyone of these titles will take you back in time to a fun and romance filled period.

Missy is a big fan of comedies and in particular loves to watch 80’s romantic comedy films such as the titles noted above. When she’s not in front of her TV, she writes online for a life insurance quotes service provider on the web.