While at Goodson-Todman, he served as producer of The Price Is Right with Bob Barker from 1972 until 1978 and also created the game show Double Dare with Alex Trebek for CBS, which ran for a short time in 1976 (not to be confused with the later, unrelated show that premiered a decade later on Nickelodeon with Marc Summers).

was canceled in May 1980 after a thirteen month run, and Wolpert did not return to television with a series until January 1983, despite shooting several pilots in the interim.

Debuting on January 4, 1988, in place of The $25,000 Pyramid with Dick Clark, the Bob Goen-hosted Blackout ended after thirteen weeks of episodes and was replaced by a revival of Family Feud with Ray Combs (which began airing on July 4, 1988); new episodes of The $25,000 Pyramid aired for thirteen weeks after Blackout's cancellation.

Rodeo Drive ended its run on August 31 of that year; the show had aired twelve weeks of new episodes prior to that and had been in reruns until the program was removed from Lifetime's lineup.

The other was Shopping Spree with Ron Pearson, which ran for nearly two years and was Wolpert's longest-running game show in his company's history.

Wolpert turned to screenwriting, penning the script for The Count of Monte Cristo (2002) and receiving a story credit for all films of the Pirates of the Caribbean series.

His minimal acting experience included playing the OB-GYN in Father of the Bride Part II who tells Diane Keaton's character Nina Banks (née Dickerson) that she is pregnant.