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Jon Cryer Is a Regular at the Emmys: See All His Looks Over the Years

Jon Cryer has a lengthy history with television's biggest awards show.

By Jill Sederstrom

Extended Family’s Jon Cryer has officially returned to the small screen with the NBC sitcom. And while it's too soon for him to be receiving any awards for the role yet, if it happens, it wouldn't be the veteran actor’s first time at the Emmys.

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As one of Hollywood’s most popular leading men in television comedy, Cryer has attended the Emmys over the years as a seven-time nominee, presenter and of course, two-time Emmy winner for his work on the popular hit show Two and a Half Men.

In light of the upcoming Emmys awards, let's take a look back at every one of Cryer's appearances at the most prestigious television award show around.

Jon Cryer Presents at the Emmys

Jon Cryer and Charlie Sheen present an award onstage at the 56th Annual Primetime Emmy Awards

Just one year after Two and a Half Men premiered in 2003, Cryer hit the stage in 2004 with co-star Charlie Sheen to present at the 56th Annual Primetime Emmy Awards at the Shrine Auditorium.

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The pair were seen laughing it up on stage together. While Sheen opted for a more traditional black suit, Cryer switched it up with a distinctive brown suit and red tie with gold accents.

Jon Cryer and Charlie Sheen Hit the Stage to Present at the Emmys Again

Jon Cryer and Charlie Sheen present an award onstage at the 57th Annual Emmy Awards

The next year, the comedic duo were back at it again at the 57th Annual Emmy Awards, where they presented the award for Outstanding Individual Performance in a Variety or Music Program.

While still rocking a bold red tie, this time, Cryer opted for a more dramatic look by pairing a black suit with a black shirt. 

Jon Cryer Takes a Beautiful Date to the Emmys

Jon Cryer and Lisa Joyner pose on the red carpet at the 58th Annual Primetime Emmy Awards

In 2006, Cryer hit the red carpet at the 58th Annual Primetime Emmy Awards with his future wife, Lisa Joyner. Wearing an all-black ensemble with a gray tie, Cryer lovingly held Joyner’s hand as the two happily posed together. 

Jon Cryer Presents Again at the Emmys

Jon Cryer and Jennifer Love Hewitt present an award onstage at the 59th Annual Primetime Emmy Awards

Two months later, he took the stage to present at the 59th Annual Primetime Emmy Awards with actress Jennifer Love Hewitt. 

Jon Cryer Returns to the Emmys with His Wife

Lisa Joyner and Jon Cryer pose in all black on the red carpet at the 60th Primetime Emmy Awards

Cryer and his now-wife, Lisa Joyner, were spotted arriving at the 60th Primetime Emmy Awards at Nokia Theater on September 21, 2008. Cryer went with a classic look of black suit, white shirt, and black tie, proving this funny man knows how to bring his A-game. 

Jon Cryer Wins Emmy in 2009

John Cryer kisses an Emmy Award trophy at the 61st Primetime Emmy Awards

Cryer took home the win for Outstanding Supporting Actor in a Comedy Series in 2008’s 61st Primetime Emmy Awards. He later told Variety he had “zero expectation” he’d win that night, but certainly looked cozy with the new hardware in the press room as he celebrated the victory.

Jon Cryer Attends Emmys Again in 2010

Lisa Joyner holds Jon Cryer's hand as he waves on the red carpet at The 62nd Primetime Emmy Awards

Cryer waved to fans alongside his wife as he arrived at the 62nd Primetime Emmy Awards on Aug. 29, 2010. He opted for a classic suit look, while she shone in a metallic minidress.

Jon Cryer Presents at the Emmys with Ashton Kutcher

Jon Cryer and Ashton Kutcher speak onstage during the 63rd Annual Primetime Emmy Awards

Cryer and his new Two and a Half Men co-star Ashton Kutcher took the stage to present at the 63rd Annual Primetime Emmy Awards in 2011, playing into their natural onscreen camaraderie and once again delivering big laughs.

Jon Cryer Earns Second Emmy Win

Jon Cryer holds an Emmy trophy at the 64th Annual Primetime Emmy Awards.


Cryer was all smiles when he took home his second Emmy award — this time for Outstanding Lead Actor in a Comedy Series — for his work on Two and a Half Men in 2012 at the 64th Annual Primetime Emmy Awards. Cryer is one of the few actors in Emmy history to have won both a Supporting and Lead Actor Emmy for the same role.

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