| 2011 | Co-organized the Occupy Wall Street comedy rallies, lending his platform to politically engaged stand-up at a nationally covered civic moment. |
| 2014 | Co-created the comedy web series Teachers Lounge with Hollis James, playing a music teacher opposite guest stars including Jim Gaffigan, Dave Attell, and Lewis Black. |
| 2018 | Released the hour special Senior Class of Earth through Bill Burr's All Things Comedy network, marking his first full-length special outside the Comedy Central system. |
| 2020 | Dropped the free YouTube special Cut/Up, his fifth comedy special overall, filmed before live audiences and positioned as a definitive document of three decades on the NYC circuit. |
| 2023 | Toured nationally as Jim Gaffigan's opening act on the Fixer Upper Tour, playing arenas and theaters across the U.S. and Canada. |
| 2024 | Continued as the featured opener on Jim Gaffigan's Barely Alive Tour, extending a multi-year touring partnership with one of comedy's top-grossing headliners. |
| 2024 | Co-hosted the weekly podcast Ted Alexandro and Hollie Harper, a conversational comedy show reaching audiences across Apple Podcasts and Spotify. |
| 1990s | Built his stand-up foundation on the New York City circuit while working days as a music teacher in NYC elementary schools, drawing on classroom life as comedic source material. |
| 2000s | Taped two Comedy Central Half Hour Specials, joining the short list of NYC comics to headline that platform. |
| 2000s | Appeared on Late Night with David Letterman, Late Night with Conan O'Brien, Jimmy Kimmel Live, and the animated series Dr. Katz, Professional Therapist, establishing himself as a TV-circuit fixture. |
