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Conan O’Brien’s Late-Night Run Was Strange, Memorable and Uneven

A chronicle of Late Night with Conan O'Brien, its sketches, Andy Richter's departure, and the deal that brought Jay Leno back.

By mitch·3 min read
A solitary host stands before an empty studio audience, bathed in a solitary light.

Late Night with Conan O’Brien ran from September 13, 1993, to February 20, 2009, on NBC. It was the second show in the Late Night franchise, replacing David Letterman’s original run. Conan O’Brien hosted it, and Joel Godard provided the announcer’s voice. The show ran for 16 seasons and 2,724 episodes, airing weeknights at 12:37 am Eastern/11:37 pm Central.

Trailer, via Majid Andary.

The Setup

The show sat in the late-late slot, the hour after Letterman’s show had ended. That timing gave it room to be stranger than the shows around it. The formula mixed celebrity interviews, musical performances and comedy sketches, but the sketches were the star. They often involved odd walk-on characters and frequent visits from celebrity guests.

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Andy Richter served as O’Brien’s sidekick from 1993 until 2000. After Richter left, O’Brien performed alone. The show’s balance shifted toward O’Brien as the sole featured performer, and the show’s identity changed accordingly. The house band was The Max Weinberg 7, led by drummer Max Weinberg, who also played with the E Street Band.

The Sketches

The show’s comedy leaned heavily on recurring bits and guest appearances that broke the usual talk-show rules. The walk-on characters were a signature move, and the celebrity visits were frequent enough to become a habit rather than a novelty. This was a show built to stand apart from the other late-night hosts, not blend in with them.

The sketches were often strange by design, not satire or parody in the traditional sense. They were simply unusual, which made them memorable.

Andy Richter’s Departure

Richter’s exit reshaped the show. He had been a steady presence since the beginning, and his absence changed the dynamic. O’Brien performing alone shifted the show’s balance toward a solo format.

The Max Weinberg 7 continued to anchor the show’s musical identity through all 16 seasons.

The Deal to Leave

In 2004, NBC announced that O’Brien would leave Late Night in 2009 to succeed Jay Leno as host of The Tonight Show. That announcement came as part of a deal to secure a new contract. Jimmy Fallon began hosting his version of Late Night on March 2, 2009.

Date Event
September 13, 1993 First episode airs
February 20, 2009 Last episode airs
2004 NBC announces O’Brien’s exit
March 2, 2009 Fallon takes over

The show’s final years carried the weight of that transition. The audience knew the end was coming.

Our Verdict

Late Night with Conan O’Brien was a consistently strong show that occasionally reached greatness. Its best moments landed with real force, and its worst moments never sank below mediocre. The show’s willingness to push past the standard talk-show format earned it a devoted following, even if its broader appeal was limited by its niche sensibility.

The show was uneven across its run, with some seasons stronger than others. The sketch material was the engine, but the interview segments did not always match it in quality.

  • The recurring sketches were the show’s strongest asset
  • Andy Richter’s departure reshaped the show’s identity
  • The deal to leave NBC came as part of a contract negotiation
  • The show’s final years carried the weight of its ending

The show’s willingness to reject convention remains a touchstone for hosts who want to set their own terms.

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