He began his career in radio as a disc jockey in 1977, at the age of 16 years old.[2] He eventually moved to Los Angeles, California in 1987, continuing his radio career.[2]
In 1989, Wingert parodied the Escape Club song "Wild, Wild West" on the Dr. Demento radio show as "Adam West", in response to the casting of Michael Keaton as the titular character for Batman.[2] He continued to work with the radio business with Westwood One, but later left the station and would take a full-time position as an air personality with KTWV.[2] After five years, he eventually left the radio station and would pursue a career in acting and voice acting.[2] Following Kevin Conroy's passing in November 2022, Wingert posted a heartfelt story on how he cited his meeting with Conroy as a major influence on his career.[3]
Wingert currently resides in Palm Springs, California.[2] In his spare time, he enjoys collecting animation art, autographs, drawings, movie and television costumes, collectible toys and rock and roll merchandise.[2]
Ollie the Magic Bum, Old Security Guard, Professor, Zookeeper, Train Mechanic, Skater Kid, Frat Boy, Quarterback, Cockney Guy, British Guy, Animal Lover, Pimp, Carny, Hawker, Billy Bob, College Citizen, College Trash Can Victim, Seal Trapped Husband, Kona Local, London Local Skaters, Elephant Lover, Grommet, Carnie, Various
ER Doctor, Ben Franklin, Boston Skaters, Bigfoot, Imp, Tiki Man, German Security Guard, Graffiti Tagger, Aborigine, New Orleans Jester, Voodoo Doctor, Church Ladder Guy, Construction Worker, Tagger, Dancing Nerd, Pyromaniac, Bummed Out Skater, Bullfighter, Peg-Leg Captain, The Devil