When the hit sitcom Two and a Half Men first aired back in 2003, it was an overnight success. Fifty-three-year-old Jon Cryer, who played the infamous Charlie Harper's (Charlie Sheen) brother, is not the preppy, clean-shaven man we came to know and love. Gone are the carefully ironed chinos and sensible shoes, Cryer has upped the bad-boy factor and now sports a shaven head and sexy stubble.
For more than eight seasons, Cryer played unlucky-in-love "Alan", who was somewhat invisible next to serial womaniser "Charlie" and heartthrob "Walden". In real life, too, Sheen (52) and Kutcher (40) recieved more attention then Cryer ever did, although we think he's fabulous!
Cryer confesses all in his book So That Happened: A Memoir
Cryer published a memoir about his life and career in 2015, which also revealed some juicy details about what it was like to work with Charlie Sheen, as well as offered an insight into his friendship with co-star Kutcher's ex-wife Demi Moore (55).
He recently starred in the film Losing It and the TV series Robot Chicken and Justic League Action. Cryer has been married to journalist and TV presenter Sara Trigger since 2007, with whom he adopted his daughter in 2009.