Originally a nightclub singer and entertainer, he has hosted and announced a number of game shows from various eras, dating as far back as the 1950s.

He never sang opera independently, but was the regular vocalist with Shelly Harmon and His Orchestra, a group that toured the Virginia area.

[2] A few years after graduating from high school, Gilbert resided in Florida for three months working as an emcee, during which he received on-the-job training and learned to walk on stage, speak in front of a public crowd, and tell jokes and stories.

[2] The Dead End Kids, a group comprising young actors such as Leo Gorcey, Huntz Hall, and Gabriel Dell, were organizing a revue.

[2] In the 1950s, Gilbert joined the United States Army's Seventh Army Special Services in Germany,[1] and was cast as the lead in Xanadu: The Marco Polo Musical, an original musical comedy inspired in part by the Samuel Taylor Coleridge poem Kubla Khan, which chronicles Marco Polo's trip to China.

[7] Gilbert went to New York City, where he quickly signed with the William Morris Agency and in 1958 received his first job on national television—as the host of a newly created game show, Music Bingo.

[2] After his year-long run on Fast Draw, Gilbert was contacted by Bing Crosby Productions to host the game show Beat the Odds, produced in Los Angeles by Bill Carruthers.

[8] In 1963, Gilbert was selected by Mark Goodson to replace Don Pardo as the announcer and audience host for the original Bill Cullen-hosted version of The Price Is Right when it moved from NBC to ABC.

[9] Gilbert also served as the announcer and audience host for Dinah Shore's syndicated daily talk show, which ran from 1974 to 1980.

[12] As audience host, Gilbert handles warm-up duties, exciting the crowd before the commencement of taping.

Other game shows for which Gilbert has announced over the decades include The $1,000,000 Chance of a Lifetime,[2] The $25,000 Pyramid, The $100,000 Pyramid, Anything for Money,[2] Blackout, Camouflage, Chain Reaction, Dream House, Every Second Counts, Fantasy, Go, Headline Chasers (produced by Griffin), Jackpot, Jeopardy!

He substituted for Gene Wood on several Goodson-Todman game shows, including Family Feud, the CBS version of Card Sharks, and Child's Play.

He succeeded Rich Jeffries (another part-time substitute for Wood) as permanent announcer of Chuck Woolery's game show Love Connection during the 1988–89 season.