After a brief unsuccessful stint at the University of South Florida, Boosler worked as doorman at The Improvisation comedy club in New York for three years, and it was there that she met comedian Andy Kaufman, a regular at the club, who convinced her she should do standup comedy. The two dated for three years and remained friends until Kaufman's death. Boosler credits Kaufman for her "comedy education" as well as her other peers at the time which included Freddie Prinze, Jay Leno, Larry David, Richard Lewis, Richard Belzer, Jimmie Walker and Ed Bluestone.
Boosler was an instant success in a field which was then still dominated by male performers. In 1986 Boosler became the first female to get her own comedy special on cable when Showtime aired "Party of One". Boosler had to save her money and produce the special herself, because none of the cable networks thought people would tune into to see a female do an hour of comedy. People magazine gave it an ‘A’. John J. O’Connor in the New York Times wrote, ”how refreshing, a woman who doesn’t have to tear her own skin off for our amusement. . an attractive human being simply standing there being funny, the first to feel she doesn’t have to be a grotesque..”
Following the rave reviews, Showtime immediately gave her a deal for three more specials, and rival HBO announced its own new series of specials, “Women of the Night”. For this reason, Boosler is widely credited with opening new doors to women in comedy.
To date, Boosler has done seven cable specials. Her one hour standup comedy concert specials for Showtime include: “Party of One”, “Broadway Baby”, “Top Tomata”, broadcast live from Omaha and voted Best Comedy Special of the Year by readers of Cable Guide magazine, and “Live Nude Girls”. Her new year’s eve comedy-variety special, “Elayne Boosler’s Midnight Hour”, was a 90 minute special done at Town Hall in New York and telecast live on Showtime. Elayne has also written, directed, and acted in two half hour movies for Cinemax; “Comedy From Here”, a drama, and “The Call”.