| 1966 | Graduated from Middlebury College in Vermont, where he had been composing irreverent musical pieces for his fraternity, planting the seed for what would become a 50-year career in adult comedy. |
| 1974 | Pivoted to adult material at a Rochester-area show, adding a set of original dirty songs that drew an eruption of audience response and set the course for his entire subsequent career. |
| 1975 | Released the album 'Hotel Buffalo,' one of his earliest full-length recordings, documenting the bawdy piano-cabaret act he was perfecting in clubs across Western New York. |
| 1978 | Released 'Concerto for Piano Voice and 566 Screaming Assholes,' a live recording title that summarized his relationship with his audience: participatory, loud, and cheerfully obscene. |
| 1982 | Released 'Sit On A Happy Face,' continuing his prolific run of studio albums that made his signature songs like 'Puff the Magic Tampon,' 'Barnacle Bill,' and 'Roll Your Leg Over' staples of the college and club circuit. |
| 1997 | Released 'Butts Up Doc!,' adding to a catalog that spanned more than two decades and kept his white tuxedo, derby, and bow tie act filling rooms from clubs to college auditoriums. |
| 2012 | Released 'Older and Dirtier,' confirming that the man Andrew Dice Clay once admitted made him look tame had no intention of cleaning up his act as he entered his late 60s. |
| 2022 | Still headlining his full raunchy variety show in his late 70s, performing the call-and-response obscenity rituals with faithful audiences who know every punchline and yell them back anyway. |
| 2023 | Marked 50 years of performing as Dr. Dirty, a half-century built on the premise that nothing and no one is sacred and that a night of belly laughs demands exactly that. |
| 2025 | Performed live shows including a date at the Andiamo Showroom in Warren, Michigan, still in trademark white tuxedo and derby, proving the act built in 1974 Rochester requires no retirement date. |