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During the same time, Shepard began appearing in more films and landed his first main character role in Let's Go to Prison (2006), alongside Will Arnett and Chi Mc Bride.

He also had a main role in the 2008 comedy Baby Mama, starring opposite Tina Fey and Amy Poehler.

When the show had its 2012 revival, he continued to appear.

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He portrayed Crosby Braverman in the NBC comedy-drama series Parenthood from 2010 to 2015.

Since 2018, he has hosted the popular podcast Armchair Expert.

He has served as their official Master of Ceremonies, along with his friend Tom Arnold, for the Inner-City Games and Hollenbeck Youth Center's Miracle on 1st Street Toy Giveaway Program in East Los Angeles.

3: "Paranormal Activity: The Marked Ones" (Paramount) --Although it's technically not "Paranormal Activity 5," the latest entry in the found-footage horror franchise focuses on a Latino teen who becomes possessed by a malevolent spirit after making the cardinal horror movie sin of investigating a crime scene. 3: "The Best Offer" (Warner Bros.) -- Geoffrey Rush plays an eccentric European art auctioneer who develops an obsession with an heiress who hires him to auction off the large collection of art and antiques left to her by her parents.

Shepard met actress Kristen Bell, also a native of Detroit's northern suburbs, at the birthday party of a mutual friend (Michael Rosenbaum); they began dating in late 2007.

The couple announced their engagement in January 2010.He also had a supporting role in the 2010 romantic comedy film When in Rome, which also starred his future wife Kristen Bell.From 2010 to 2015, Shepard was part of the main cast of the NBC drama Parenthood, playing Crosby Braverman.Shepard wrote the script for the Paramount venture Get 'Em Wet, in which he again appeared with Arnett.In 2010, he wrote, directed and starred in the low-budget satirical mockumentary feature Brother's Justice; the film won an Audience Award at the 2010 Austin Film Festival.Featured guests on the show have included Kristen Bell, Ashton Kutcher, and Joy Bryant.