| 1995 | Performed on 'Late Night with David Letterman,' where Letterman, recognizing something singular in Romano's persona, offered him a development deal with his production company on the spot. |
| 1996 | Launched 'Everybody Loves Raymond' on CBS, the sitcom that grew from Letterman's deal; Romano would win three Primetime Emmy Awards for the show, one as lead actor in 2002 and two as executive producer when it won Outstanding Comedy Series in 2003 and 2005. |
| 2002 | Became the highest-paid actor in television history for his role as Raymond Barone, a benchmark that underscored the show's dominance in the CBS prime-time lineup. |
| 2002 | Voiced Manny the woolly mammoth in Blue Sky Studios' 'Ice Age,' beginning a franchise voice role he would reprise across sequels for two decades. |
| 2009 | Created and starred in 'Men of a Certain Age' on TNT, a critically praised comedy-drama that ran two seasons and showed a dramatically quieter register than 'Everybody Loves Raymond.' |
| 2017 | Co-starred in Judd Apatow's 'The Big Sick' alongside Kumail Nanjiani, bringing his understated dramatic style to one of the year's most acclaimed comedies. |
| 2019 | Delivered a career-high dramatic turn as mob lawyer Bill Bufalino in Martin Scorsese's 'The Irishman' alongside Robert De Niro and Al Pacino, and starred in the Netflix comedy 'Paddleton' opposite Mark Duplass. |
| 2023 | Made his directorial debut with 'Somewhere in Queens,' a working-class Italian-family comedy he co-wrote with Mark Stegemann; the film premiered at the Tribeca Film Festival and was released nationally through Lionsgate and Roadside Attractions. |
| 2026 | Made his Broadway debut in Simon Rich's 'All Out: Comedy About Ambition,' produced by Lorne Michaels and directed by Tony Award winner Alex Timbers, performing alongside Nicholas Braun, Jake Shane, and Jenny Slate. |
| 2026 | Reunited with the 'Everybody Loves Raymond' cast at the ATX TV Festival in Texas for a 30th-anniversary celebration of the Emmy-winning series, alongside creator Phil Rosenthal and the original writing team. |