| 1986 | Self-financed and aired 'Party of One' on Showtime, becoming the first female comedian to headline an hour-long comedy special on cable television after network executives refused to greenlight it. |
| 1988 | Rolling Stone dubbed her 'The First Lady of Standup Comedy', recognizing her as the defining female voice in a male-dominated era of the form. |
| 1991 | Delivered her Showtime special 'Live Nude Girls', the fourth in a run of Showtime specials that followed 'Party of One' and set a new bar for women in long-form stand-up. |
| 1993 | Performed at the White House Correspondents' Dinner during President Clinton's first year in office, one of the most visible platform bookings in American comedy. |
| 1993 | Wrote city-by-city customized material for Barbra Streisand's tour and hosted the game show 'Balderdash', adding television hosting to a career already spanning HBO, NBC, and Showtime. |
| 2001 | Founded Tails of Joy, her non-profit animal rescue organization that channels resources to the smallest, neediest rescue groups and individual cases nationwide. |
| 2017 | Included on Rolling Stone's '50 Best Stand-Up Comics of All Time' list, placing her among a handful of women recognized in a field dominated by male acts across decades. |
| 2019 | Returned to the New York stage at 'Laughing Liberally: Make America Laugh Again' at Theatre at St. Clement's alongside Janeane Garofalo and Judy Gold. |
| 2022 | Released 'Elayne Boosler: Timeless', a boxed set collecting four of her iconic Showtime specials plus a new CD, making her foundational catalog available for a new generation. |