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Jon Cryer Had the Sweetest Two And A Half Men Reunion at the Emmys

The actors reprised their roles as Alan Harper and his mother, Evelyn, from Two And A Half Men to present an award at the 75th Emmy Awards.

By Caitlin Schunn

Jon Cryer is back on television with the new NBC sitcom, Extended Family, as he plays Jim, who is navigating co-parenting with his ex-wife, Julia (Abigail Spencer), and her new boyfriend, Trey (Donald Faison). But despite being busy with his new role, Cryer still paid homage to one of his most well-known television sitcom characters during a Two and a Half Men reunion at the 75th Emmy Awards.

Jon Cryer and Holland Taylor Reunite at The Emmys

How to Watch

Watch Extended Family Tuesdays at 8:30/7:30c on NBC and next day on Peacock.

As the familiar “men, men, men, men, manly men, men, men” opening tune to Two and a Half Men rang out at the Emmys, Cryer, who played Alan Harper on the comedy, walked out with actress Holland Taylor, who played Evelyn, Alan’s mother, on the Emmys stage. The two starred in all 12 seasons of the show together.

“Like a good bra, a supporting actor makes things look effortless, while secretly holding up the whole show,” Taylor said to the audience, with the first joke of the on-stage reunion.

It immediately became clear the two were acting in their famed Two and a Half Men roles.

“You know, Mom, I actually won this award, so you could say I’m a good bra,” Cryer replied.

Cryer was nominated for the Emmy for Outstanding Supporting Actor in a Comedy Series for his portrayal of Alan Harper in 2006, 2007, and 2008, before winning the Emmy in 2009. He was nominated again in 2010 and 2011, and then won the Emmy for Outstanding Lead Actor in a Comedy Series in 2012.

“Well, Alan, darling, I don’t think I would ever say that,” Taylor replied during the 75th Emmys. “And I certainly hope none of our nominees for Supporting Actor in a Comedy Series would either.”

RELATED: Everything to Know About Abigail Spencer's Real-Life Family Ahead of the Extended Family Premiere

The mother-and-son duo then announced that Ebon Moss-Bachrach won for his role on The Bear at the Emmys.

Taylor and Cryer went on to do other projects together, even before Two and a Half Men went off the air after 12 seasons in 2015. Ann, the one-woman Broadway show starring Taylor, went on a run from Feb 2013 to June 2013, with 19 previews and 132 regular performances. It was described as “an intimate, no-holds-barred portrait of Ann Richards, the legendary Governor of Texas,” according to Playbill. Cryer and his wife, Lisa Joyner, were producers on the show.

Live theater is in Cryer’s blood, actually. His mother, Gretchen Cryer, is best known for the 1978 long-running off-Broadway musical I’m Getting My Act Together and Taking It on The Road. She also directed her son in True Stories, a series of solo shows that ran off-Broadway in May 2022. Cryer’s play, called The Actor’s Nightmare, was a “personal love letter to theatre,” according to Playbill.

“Needless to say, working with my son, Jon Cryer, as he makes his maiden voyage into this kind of theatre is another dream come true,” she told Playbill.

Watch new episodes of Extended Family with Cryer on Tuesdays at 8:30/7:30c on NBC, and the next day on Peacock.

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