Jon Cryer’s First Sitcom Took Place at UTA

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Cryer had landed a CBS deal off the success of Pretty in Pink, but producer Richard Dubin preferred another on-the-rise actor, Ben Stiller, who also auditioned. “I thought that Jon, while a very able and journeyman actor, didn’t have the cojones necessary for [Teddy],” Dubin tells The Hollywood Reporter. 

This was Wilson and Dubin’s third project together, but it led to a falling-out, with Dubin leaving before shooting wrapped. Tension spiked over Lainie Kazan (My Favorite Year), Dubin’s pick as Teddy’s mom. After seven episodes, Wilson wasn’t happy with Kazan and let her go, and scenes were reshot. (Erica Yohn replaced Kazan as Teddy’s grandmother.)

Jane Sibbett, later known as Carol on Friends, played Cryer’s love interest, and they dated during that time. Cryer says that the show’s turbulence brought them together: “It was a roller coaster, and when you’re both on the same roller coaster, you tend to grab each other.” 

Critics praised Teddy Z — THR dubbed it “this season’s best new comedy” — and co-star Alex Rocco would win a supporting actor Emmy for his turn as agent Al Floss. But low ratings led to the series being pulled midseason with five episodes unaired.

“It was absolutely devastating, and I really took it personally,” recalls Cryer. Now, he looks back on the show fondly: “The effort was worth it, even if it didn’t hit all the right notes.”

This story appeared in the Oct. 30 issue of The Hollywood Reporter magazine. Click here to subscribe.