Challenges Faced by Conan O'Brien: Obstacles and Turning Points

By Popular Timelines Editorial Team · Updated: March 14, 2026

Life is full of challenges, and Conan O'Brien faced many. Discover key struggles and how they were overcome.

Conan O'Brien is a prominent American television host, comedian, writer, and podcaster recognized for his career in late-night television. He gained fame hosting Late Night with Conan O'Brien, The Tonight Show with Conan O'Brien, and Conan. Prior to hosting, O'Brien wrote for Saturday Night Live and The Simpsons. In recent years, he's expanded his career with the podcast Conan O'Brien Needs a Friend, and the travel show Conan O'Brien Must Go. O'Brien's comedic style and interviewing skills have made him a well-known figure in entertainment.

Sections (5)

Full Timeline Early Life & Education Career & Achievements Success & Recognition Challenges & Struggles

1991: Quit Saturday Night Live

In 1991, Conan O'Brien quit "Saturday Night Live", citing burnout after the failure of his sitcom and an engagement that fell through.

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September 13, 1993: Premiere of Late Night with Conan O'Brien

On September 13, 1993, "Late Night with Conan O'Brien" premiered to unfavorable reviews from contemporary critics.

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1994: Threats of Cancellation

In 1994, "Late Night with Conan O'Brien" was constantly at risk for cancellation; at one point, NBC threatened to put him on a week-to-week contract.

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January 1995: Robert Smigel Quit as Head Writer

In January 1995, Robert Smigel quit as head writer of "Late Night with Conan O'Brien", feeling burned out.

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September 2006: Stalking by Father David Ajemian

Starting in September 2006, Conan O'Brien was stalked by Father David Ajemian, who sent O'Brien letters signed as "your priest stalker."

2007: Andy Barker, P.I. Series

In 2007, Conan O'Brien executive produced and co-wrote the pilot for the NBC adventure/comedy series Andy Barker, P.I., starring Andy Richter. Despite being named one of the Top Ten Shows of 2007 by Entertainment Weekly, the show was canceled after six episodes due to low ratings.

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April 8, 2008: Ajemian Guilty Plea

On April 8, 2008, Father David Ajemian pleaded guilty to stalking Conan O'Brien.

September 25, 2009: Concussion on The Tonight Show

During the taping of The Tonight Show on September 25, 2009, Conan O'Brien suffered a mild concussion after slipping and hitting his head during a comedy sketch with Teri Hatcher. He was examined at a hospital and released the same day.

November 2009: Declining Ratings for The Tonight Show

By November 2009, ratings for Conan O'Brien's The Tonight Show had declined by approximately 2 million viewers compared to the previous year when Jay Leno was the host.

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January 7, 2010: NBC Discusses Moving Leno Back to Late Night

On January 7, 2010, NBC executive Jeff Zucker met with Jay Leno and Conan O'Brien to discuss moving Leno out of prime time and back into late night. The proposal involved O'Brien remaining as host of The Tonight Show at 12:05 am, with Leno hosting a 30-minute show at 11:35 pm.

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January 21, 2010: Agreement to Exit The Tonight Show

On January 21, 2010, it was announced that Conan O'Brien had reached a deal with NBC to exit The Tonight Show the next day. The agreement included a $45 million payment, with $12 million allocated for distribution to his staff.

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May 2, 2010: 60 Minutes Interview

After being prohibited from television appearances, Conan O'Brien spoke about the Tonight Show conflict on 60 Minutes on May 2, 2010. He discussed the sudden and violent end to his tenure and his feelings about NBC's decision.

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