Image: Newsmakers / Stephen Shugerman/Getty Images for AFI
Image: Getty Images/Newsmakers / Stephen Shugerman/Getty Images for AFI

Fame is a funny old thing. One minute, actors can be riding an unprecedented wave of adulation and acclaim. But what seems like moments later, they’ll be struggling to maintain their place in the spotlight and scrabbling for whatever meager roles they can find. And while some stars have enjoyed incredible longevity in Hollywood, others haven’t proved as lucky. Indeed, it seems like most agents have scratched these once high-profile names off their casting lists.

Image: Jeff J Mitchell/Getty Images
Image: Jeff J Mitchell/Getty Images

20. Sean Connery

As the first actor to play James Bond, Sean Connery will always have a special place in cinema history. However, the star’s later roles left fans neither shaken nor stirred and the 2003 failure of The League of Extraordinary Gentlemen convinced Connery to abandon the business for good. Connery’s only film part since was a voice role in 2012’s Sir Billi.

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Image: Jemal Countess/Getty Images
Image: Jemal Countess/Getty Images

19. Freddie Prinze Jr.

Once the king of ’90s comedies, Freddie Prinze Jr. set teen hearts racing with hits like 1999’s She’s All That. Unfortunately, the star’s charisma waned in the following decade and a series of flops – most notably 2008’s atrocious Delgo – marked the end of his life as a leading man. These days, Prinze mainly does voice work for cartoons and video games.

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