Conan O'Brien at the American Museum Of Natural History Gala. (Photo: Evan Agostini / Getty Images)

Because of his witty, self-effacing comedic style, Conan O’Brien rose to the top of late night television fame as host of NBC’s “Late Night with Conan O’Brien” (1993- ). Even before landing that high-profile gig, this tall – he was 6 feet 4 inches – gangly, carrot-topped comic was already revered in certain circles for his writing and producing talents on such comedy stalwarts as “Saturday Night Live” (NBC, 1975- ) and “The Simpsons” (Fox, 1990 -). Despite a shaky start in 1993 – many predicted he would be replaced by year’s end and most had no idea who he even was – O’Brien not only persevered, but thrived, thanks to his sharp monologues, outlandish skits and easy rapport with former co-host Andy Richter. The host quickly developed a large, devoted college-aged following which helped O’Brien develop into a household name. Wider recognition meant more opportunity – after hosting the 2002 Emmy Awards, he was named to succeed Jay Leno as host of “The Tonight Show,” seemingly assuring O’Brien’s stature as a late night heavyweight. Sadly, after taking over his dream job, he was forced to step down after his own program's low-ratings and NBC's poor scheduling and ineffective management led him to leave the show after only seven months and a relocation from New York to Los Angeles. His perceived mistreatment by the network after over 15 years of service, made O'Brien the underdog to his perceived villain, "Tonight Show" replacement, part deux, Jay Leno. The January 2010 late night scandal – tagged "Conan-Gate – ignited the ire of Conan's rabid "I'm with Coco" fans, who took to social networking sites and street protests in support of their late night hero, while fellow comics weighed in, with most in support of O'Brien, whose next move became one of the hottest topics of the new year. Whatever O’Brien’s future held, his legacy of melding together frat-boy foolishness with intelligent, twisted writing remained unparalleled, leaving his late night legacy intact.

Born Apr. 18, 1963 in the Boston suburb of Brookline, MA, O’Brien was the third child of six in his Irish-American family. The son of Dr. Thomas O’Brien, a research physician and associate professor at Harvard Medical School, and Ruth Reardon O’Brien, a former lawyer, young O’Brien graduated as valedictorian from Brookline High School and went on to attend Harvard University. As an undergrad at the prestigious university, he wrote for the school’s legendary humor magazine, The Harvard Lampoon, of which he also served as president during his sophomore and junior years. In 1985, O’Brien graduated magna cum laude with a bachelor’s degree in American History and Literature.

After graduating Harvard, O’Brien moved to Los Angeles, where he joined the writing staff of the HBO series, “Not Necessarily the News” (1983-86), for which he wrote regularly for two years. While on the series, O’Brien also found time to act in improvisational skits, most notably for the Los Angeles-based comedy troupe, The Groundlings. In 1988, O’Brien’s comedic writing talents caught the eye of “Saturday Night Live” (NBC, 1975- ) executive producer Lorne Michaels, and he was soon hired on as a writer for the infamous late-night comedy show. O’Brien wrote three-and-a-half years worth of “SNL” sketches, penning the popular recurring bits, “Mr. Short-Term Memory,” “The Girl Watchers” and sketches featuring Dieter, the androgynous West German talk show host played by Mike Myers. His most notorious "SNL" moment was writing the now infamous nude beach skit where "penis" was uttered 60 times. His efforts paid off when he and his fellow “SNL” writers shared an Emmy Award in 1989 for Outstanding Writing in a Comedy or Variety Series.

O’Brien left “SNL” in 1991 to write and produce the somewhat infamous television pilot that never was, “Lookwell” (NBC, 1991), which starred Adam West as a former star of a cancelled TV cop show who continued to try to solve crimes. The pilot aired that July but was not picked up as a series. Later that year, O’Brien was hired on as a writer and producer for the Fox animated series, “The Simpsons” (FOX, 1989- ). So impressive were his talents, he was soon promoted to supervising producer and worked on the series for two years. During those years, O’Brien penned what many believe to be the best "Simpsons" episode of all time – certainly, it was O’Brien’s favorite – “Marge vs. The Monorail.” The 1993 fourth-season classic was a song-filled take-off on “The Music Man” and featured the guest voices of Phil Hartman as a fast-talking monorail salesman and Leonard Nimoy as a stuffy, enigmatic version of himself.

Around this same time, another opportunity was presented, one that eclipsed O'Brien's success on both “SNL” and “The Simpsons.” In April, 1993, he seemingly came out of nowhere to win the coveted hosting slot as David Letterman’s successor on NBC’s “Late Night with…” (NBC, 1982- ). Comic Andy Richter was hired on as O’Brien’s sidekick and Bruce Springsteen drummer, Max Weinberg, was brought on as the show’s new Paul Schaffer-esque music director. Though the series first received poor ratings and rumors of cancellation rumbled through the halls of 30 Rockefeller Plaza, O’Brien’s wacky and self-deprecating style of comedy eventually caught on. Dubbed “Late Night’s King of Cool” by Entertainment Weekly, O’Brien and staff delivered with sketches like “The Masturbating Bear,” “In the Year 2000,” and “Pimpbot 5000” – to say nothing of introducing the world to Triumph the Insult Comic Dog. Over the years, O’Brien and the “Late Night” writing team consistently garnered Emmy and Writer’s Guild Award nominations for Outstanding Writing in a Comedy or Variety Series, including two consecutive WGA wins in 2002 and 2003.

With his success in late-night TV, O’Brien formed his own production company, Conaco, in 2001 which shared productions credits on “Late Night.” During his “Late Night” run, O’Brien also appeared as a guest on the series “The Single Guy” (NBC, 1995-97), “Spin City” (ABC, 1996-2002), and “Andy Richter Controls the Universe” (FOX, 2002-04). In 2002, host O’Brien delivered what many considered the Emmy Award’s funniest opening monologue in its televised history. Due to his continued critical success and devoted late night fan base, it was announced to much fanfare in 2004 that the now iconic redhead would take over for Jay Leno as host of NBC’s “The Tonight Show” (1992- ) upon Leno’s retirement from the show in 2009. In late 2007, NBC-Universal President and CEO Jeff Zucker confirmed the network’s commitment to O’Brien after rumors of Leno perhaps having second thoughts about leaving “The Tonight Show.” At the same time O'Brien was relishing NBC's continued committment to him and his gang of merrymakers headquarted at 30 Rock, the comic found himself on the receiving end of a stalking incident, involving of all things, a Catholic priest obsessed by him. The threats, which were publically leaked, were considered serious enough that the police got involved to ensure his safety.

Then news came that the ever-reticent Leno was gunning for a 10 pm slot as lead-in, yet again, to O'Brien. He was granted the gig and many saw this as a slap in the fact to new "Tonight Show" host. If anyone took offence, nothing was spoken publicly, unlike Leno's earlier squirmishes with the ever vocal and often cranky Letterman. By the time O'Brien bid farewell to "Late Night" and his masturbating bear in May 2009, many fans reacted to his departure from “Late Night” as a kind of death. O'Brien, in his final, somewhat emotional sign-off, assured his viewers he would still be the same "childish assh*ole" they had grown to love over 16 years. After "SNL" comic Jimmy Fallon took over "Late Night" to somewhat lackluster reviews, O'Brien took a few months off to relocate and acclimate to his new L.A. life, as well as prepare his new show. By the time "The Tonight Show with Conan O'Brien" premiered to much fanfare on June 1, 2009, fans were ready and willing to say goodbye to Jay and welcome the hipster-dufus and his off-beat comic brilliance to the most envied gig in television history.

Unfortunately, after only a few months on the air, it became apparent that "The Tonight Show" ratings were down with O'Brien at the helm. The biggest news the show made was when O'Brien suffered a concussion after a taped segment gone wrong, in which he ran a marathon with Terri Hatcher and promptly slipped on stage when crossing the finish line, hitting his head hard. He was taken to the hospital immediately after he began showing signs of memory loss. He recovered quickly, but the worst was yet to come later that fall when it became apparent to NBC and its affiliates that the Leno 10 pm experiment was an unmitigated disaster. Knowing the end was near, Leno expressed interest in returning to his old gig at 11:30 pm and by January 2010 – after O'Brien's show had had only seven months to find its footing – NBC announced the official cancellation of Leno's program.

What that would mean for "The Tonight Show" host was the subject of much speculation in the media and by outraged fans who felt O'Brien was getting the shaft by his own network and with the help of Leno, in much the same way Letterman had years before. Online chatter leaned predominately toward the O'Brien camp, with NBC boycotts being bandied about. In the end, O'Brien could stay at the network as host of "The Tonight Show," but be bumped back to midnight and still have Leno as a lead-in – perhaps one of the many reasons his own show had suffered in the first place. Or he could leave the network for a better deal, armed with a rumored $25-$50 million payout. Fans waited breathlessly for O’Brien’s decision. They did not have to wait long. On January 12, O'Brien released an official statement heard 'round the world, in which he rejected NBC’s attempt to move “The Tonight Show” to the post-midnight slot to accommodate Leno’s return to late-night, stating he could not "participate in what I honestly believe is its ("The Tonight Show") destruction... So it has come to this: I cannot express in words how much I enjoy hosting this program and what an enormous personal disappointment it is for me to consider losing it." After two weeks of O'Brien's bitter but often funny mud-slinging directed at Leno and NBC, it was announced he had sealed a $45 million deal to leave the show, with the host pocketing $33 million and the staff splitting the $12 million.