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From an '80s Teen Star to Today, See Jon Cryer Over the Years: Photos

Emmy winner Jon Cryer has been acting for more than 40 years. Every picture tells a story about his acclaimed career.

By Joe Dziemianowicz

He’s back and ready to crack us up again!

How to Watch

Watch Extended Family on NBC and Peacock.

Emmy winner Jon Cryer has brought his quick wit and easygoing comedic touch in his roles ever since his movie debut 40 years ago. Naturally, he's in his comfort zone in the new NBC series Extended Family, which takes a lighthearted look at a couple who are amicably divorced and coping with challenges of co-parenting and blending families. Cryer stars with Abigail Spencer, who plays his ex-wife, and Donald Faison, who plays her fiancé.

Before we watch Cryer's return to the small screen, get to know more about Cryer’s career through the years in pictures.

1984: Jon Cryer makes his movie debut in No Small Affair 

Jon Cryer in publicity portrait for the film 'No Small Affair'

Like many actors, Cryer got his acting start on stage. After appearing in the Broadway productions of Torch Song Trilogy and Brighton Beach Memoirs, he made his big-screen debut in No Small Affair. He played a teenage photographer who falls for a woman played by Demi Moore who accidentally ends up in one of his snaps. Today, that’s called photobombing!

1986: Jon Cryer breaks through in Pretty in Pink

Jon Cryer, Molly Ringwald and Andrew McCarthy on set of 'Pretty In Pink'

In this high school rom-com by filmmaker John Hughes, Cryer stepped up as Phil "Duckie" Dale, the adoring BFF to Andie, played by Molly Ringwald. He competed for Andie's affections against cool guy Blane (Andrew McCarthy).

The role gave Cryer a shot to fire off frequent zingersHis name is Blane?” gasps Duckie at one point. “Oh! That's a major appliance, thats not a name!The film was a box office hit, partially thanks to Duckie's charm. Fans still debate whether Andie really ended up with the right boyfriend.

1989: Jon Cryer makes the leap to prime time

Jon Cryer as Theodore "Teddy" Zakalokis in "The Famous Teddy Z"

Cryer parlayed his movie success into prime-time star vehicles including The Famous Teddy Z, which was about a talent agent and ran for a season. Other shows followed, including Partners, about architects that launched in 1995, and the therapy-themed The Trouble with Normal, which began and ended in 2000.

2003: Two and a Half Men begins a 12-year run

Jon Cryer, Angus T. Jones and Charlie Sheen pose for promotional images for Two and a Half Men

In this blockbuster sitcom hit, Cryer played Alan, an uptight divorced dad with a mischievous son, Jake (Angus T. Jones), who moved in with Alan’s freewheeling jingle writer brother Charlie (Charlie Sheen) in Malibu. As the trio navigated relationships and careers, comedic chaos ensued.

RELATED: Jon Cryer Returns to TV: Why He Said Yes to NBC’s “Incredibly Unusual” Sitcom Extended Family

Cryer appeared in Two and a Half Men from Sept. 2003 to Feb. 2015. Along the way he was nominated seven times for an Emmy. In 2009, he won for Outstanding Supporting Actor in a Comedy Series, and in 2012, he won for Outstanding Lead Actor in a Comedy Series.

2011: Jon Cryer gets a star on the Hollywood Walk of Fame

Jon Cryer lays on the floor at his star ceremony

When Cryer received the 2,449th star in 2011, Two and a Half Men creator Chuck Lorre along with co-stars Ashton Kutcher, who joined the show after Sheen left, and Angus T. Jones were there to cheer him on.

2015: Jon Cryer tells his story

Jon Cryer attends 92nd Street Y Presents: Back on Broadway: Kristin Chenoweth And Peter Gallagher

In his 2015 memoir, So That Happened, Cryer chronicles his 30-year career in theater, film, and TV. He also recalls growing up in New York as the child of two actors and artists.

Considering that Cryer’s career is still going strong, he may need to follow-up at some point with a sequel such as So That Happened Too.

2023: Jon Cryer is a real-life Family man

Lisa Joyner and Jon Cryer smile together as they attend a red carpet

Like every actor, Cryer’s personal experiences inform his roles, including his newest one on Extended Family.

Cryer married entertainment reporter Lisa Joyner in 2007 in Mexico, and the couple adopted a baby girl, Daisy, two years later.

Cryer also has a son from his previous marriage to Sarah Trigger, which ended in divorce in 2004, PEOPLE reported.

Extended Family premiered Saturday, December 23rd at 8/7c on NBC, with new weekly episodes returning Tuesday, January 2nd at 8:30/7:30c on NBC. All episodes will be available to stream the next day on Peacock.