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Wolpert's first television appearance came as a contestant on the original version of Jeopardy! in 1969. He competed in the Jeopardy! Tournament of Champions that year and won. Wolpert's upset win was notable for defeating the two highest-winning contestants in regular Jeopardy! play up to that point, Jane Gschwend and Elliot Shteir.
Wolpert began his game show-producing career working for Dan Enright in Canada. He later worked as a producer and creator of game shows for Chuck Barris Productions and Goodson-Todman Productions. While at Goodson-Todman, he served as producer of The Price Is Right from 1972 until 1978 and also created the game show Double Dare 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).
Wolpert left Goodson-Todman to form his own production company, and his first game show was the 1979 series Whew! for CBS. Wolpert produced the series with Burt Sugarman for most of its run. Whew! was canceled in 1980 and Wolpert did not return to television with a series until January 1983, despite shooting several pilots in the interim. On January 3, 1983, Wolpert's Hit Man debuted on NBC with Peter Tomarken as its host. Hit Man lasted thirteen weeks on the air.
Five years later in 1987, and after a failed syndication pilot based on the board game Trivial Pursuit (the game would get two other shows based on it, one in 1993 and one in 2008, both incorporating interactive elements), Wolpert returned to daytime television with the series Blackout for CBS. Debuting on January 4, 1988, in place of The $25,000 Pyramid, the Bob Goen-hosted Blackout ended after thirteen weeks of episodes and was replaced by a revival of Family Feud (which began airing on July 4, 1988); new episodes of The $25,000 Pyramid aired for thirteen weeks after Blackout's cancellation.
In 1990, Wolpert launched a new series on the Lifetime network based on a pilot he had shot in 1981 with Tomarken as host. On February 5, 1990, Rodeo Drive debuted with comedian Louise DuArt hosting. 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.
After a hiatus, Wolpert returned to the Goodson Productions team and produced a new The Price Is Right series for Goodson and Paramount Television. The New Price Is Right debuted in syndication in September 1994, with Wolpert producing. Ratings for The New Price Is Right were lacking,[clarification needed] resulting in a cancellation after sixteen weeks in January 1995.
In 1996 Wolpert and The Family Channel teamed up for two series. One was Wait 'til You Have Kids, a series based on The Parent Game. The other was Shopping Spree, which ran for nearly two years and was Wolpert's longest-running game show in his company's history. After Shopping Spree went off the air in August 1998, Wolpert's company stopped producing programming. He was executive producer of the 1998 version of Match Game.
In the 2010-11 season, Wolpert was listed as a consultant during the credits of Who Wants to Be a Millionaire? and had some input in that season's format changes.