In an industry where comedy careers are often measured in brief seasons or viral moments, **Paul Dinello** has maintained one of the most prolific, respected, and enduring creative journeys in American entertainment. Spanning four decades—from driving taxi cabs through Chicago’s South Side to winning multiple Emmy and Peabody Awards at the Ed Sullivan Theater—Dinello has left an indelible mark on television satire.

Below is the definitive chronological career timeline of Paul Dinello.

1962–1987: Chicago Roots and The Improv Spark

  • 1962: Born in Chicago, Illinois, to an Italian-American family.
  • Early 1980s: Attended DePaul University in Chicago, graduating with a degree in communications while driving taxi cabs and working odd jobs to support himself.
  • 1986: Began taking improvisational comedy classes at The Players Workshop and The Second City Training Center, discovering a natural gift for character-driven deadpan timing.

1988–1994: The Second City Touring Company & Mainstage

  • 1988: Hired by The Second City Touring Company, where he met lifelong creative soulmates Amy Sedaris and Stephen Colbert on an unheated Midwestern tour bus.
  • 1990–1993: Promoted to the legendary Second City Mainstage in Chicago, co-writing and performing in critically lauded revues alongside Steve Carell and Mitch Rouse.
  • 1994: Moved to New York City with Sedaris and Colbert to pitch original television projects.

1995–2000: ‘Exit 57’ and The ‘Strangers with Candy’ Breakthrough

  • 1995–1996: Co-created, wrote, and starred in Exit 57 on Comedy Central, earning five CableACE Award nominations.
  • 1999–2000: Co-created, wrote, and starred in Strangers with Candy as art teacher Geoffrey Jellineck. The series became a massive cult phenomenon and transformed Comedy Central’s reputation.

2001–2005: Literature, Sundance, and Directing

  • 2003: Co-authored the bestselling satirical novel Wigfield: The Can-Do Town That Just May Not and headlined a nationwide sold-out stage tour.
  • 2005: Made his feature directorial debut with the independent film adaptation of Strangers with Candy, premiering at the Sundance Film Festival to critical acclaim.

2005–2014: The Colbert Report Era

  • 2005: Joined The Colbert Report as a founding head writer and supervising producer.
  • 2005–2014: Won two Peabody Awards, multiple Primetime Emmy Awards, and made dozens of iconic recurring on-screen appearances as Tad, the building manager.

2015–Present: The Late Show with Stephen Colbert

  • 2015: Joined CBS’s The Late Show with Stephen Colbert as Supervising Producer and Senior Writer, moving production to the historic Ed Sullivan Theater.
  • 2016–Present: Helped steer The Late Show to the #1 spot in late-night television ratings for eight consecutive seasons, winning the 2021 Peabody Award.

Career Summary by the Numbers

  • Emmy Nominations: Over 35 career nominations across writing and producing.
  • Peabody Awards: 3 (The Colbert Report, The Late Show).
  • Books Published: 3 (Wigfield, Simple Times, I Am America).
  • Decades in Comedy: 4.

Archival Historical Records