[1] Stewart was one of the hosts for Town Hall Party, a Los Angeles–based country music program airing from 1952 to 1961 and carried by KFI radio and KTTV-TV television.

Let's Make a Deal host Monty Hall called Stewart "the best second banana you ever found in your life" and said that "it was a very, very good feeling between us.

In 1981, Jay was selected by Mark Goodson to announce approximately four to six weeks worth of episodes on Card Sharks, pairing him with future Sale of the Century host Jim Perry.

Besides his duties on the NBC and syndicated versions of $ale of the Century, Stewart announced the first year of Scrabble before being replaced by Charlie Tuna in 1985.

In addition, between his stints with Barry & Enright and Reg Grundy Productions, Stewart was the voice-over for National Enquirer commercials, which he continued to do until around 1986.

Stewart could not overcome the pain of his daughter's death and turned to alcohol, which ultimately led to his departure from $ale of the Century in January 1988.

He had been experiencing severe depression and he also suffered from chronic, intractable back pain for years, reportedly due to frequent heavy lifting during his work on Let's Make a Deal (Stewart had to carry prize display tables to and from the audience area whenever a game on Let's Make a Deal called for them; he would bring out the prizes, announce them, then take them back offstage when done).