Who

America's second favorite late-night talk show host, the gap-toothed Letterman has been getting medium-sized yuks for decades.

Backstory

Letterman started his career as a radio host and TV weatherman in Indianapolis, but soon turned to comedy writing after managers at the TV station got fed up with his on-air gags. (He once congratulated a tropical storm that had been upgraded to hurricane status.) In the late 1970s, Letterman worked the stand-up circuit at L.A. comedy clubs and suffered through indignities like appearing on The Gong Show in 1976 and on Mary Tyler Moore's short-lived sketch comedy show in 1978. After a few guest spots on the Johnny Carson-era Tonight Show, NBC tapped Letterman to host a morning show called The David Letterman Show. Though it lasted only four months, the program introduced audiences to Dave's sardonic approach to the talk show format (and to Stupid Pet Tricks, for whatever that's worth). NBC wasn't dissuaded by the show's cancellation, and gave Letterman his big break in 1982 when Late Night debuted following the Tonight Show.

Letterman was pegged by many to replace Carson when he retired in 1992, but the gig went to Jay Leno instead, sparking a bitter rivalry between the two late night talkers (and former close friends). In 1993, then-CBS chief Howard Stringer lured Letterman to the Tiffany network to host Late Night in the 11:30 time slot against Leno. He's consistently scored lower in the ratings ever since although how much of that has to do with Dave, his slightly offbeat humor, or CBS's lackluster primetime lineup remains an open question. The same year, Letterman set up Worldwide Pants Inc., the production company responsible for such shows as Everybody Loves Raymond, the Late Late Show with Craig Kilborn, NBC's Ed, and Strangers With Candy: The Movie, starring frequent Letterman guest Amy Sedaris.

Of note

Letterman's acerbic humor doesn't seem to play as well in Middle America as Leno's blander, more mainstream shtick. No matter—while Dave has never been able to topple Jay in the ratings, at least his checks are bigger. Letterman reportedly makes $40 million a year, which makes him the second highest-paid host on television right behind Oprah. A new contract means he'll be on air at CBS at least through 2010. But he'll have new competition beginning next year. After Leno walks off the Tonight Show stage in 2009, Letterman will go head-to-head with Leno's replacement, Conan O'Brien. 

Personal

Although he gladly hams it up before some 4.3 million viewers nightly, Letterman is guarded about his personal life. He divorced his college sweetheart, Michelle Cook, in the late '70s, and is currently engaged to longtime girlfriend Regina Lasko, with whom he has one son, Harry. Clearly Letterman has good reasons to keep private. A mentally ill stalker named Margaret Ray repeatedly broke into his house beginning in the late '80s, once falling asleep on his tennis court and another time stealing his Porsche. And in 2005, police uncovered a plot to kidnap Harry—who was then 16 months old—from Letterman's 2,700-acre Montana ranch. A painter who was working at the ranch was arrested for hatching the plot.

Health report

Letterman underwent emergency quintuple-bypass surgery in 2000, performed by cardiac surgeon Wayne Isom. (Dave has since given up coffee and cigars.) After he returned to his Late Night desk a month later, he brought his team of doctors on to the show for an emotional tribute.

Habitat

Letterman spends most of his time at his 100-year-old colonial-style home in North Salem. He bought the 88-acre property for $5 million in 1994, although he didn't move in until 2002. In 2007, he paid another $5 million for the 20-acre estate next door. Both properties feature massive homes—his main residence is 8,300 square feet; the newer one is 7,000 square feet. When those start to feel cramped, he can always retreat to his giant ranch outside Choteau, Montana, or, if he's looking for some sun, his villa on St. Bart's.

True story

Letterman has always had a reputation for being withdrawn in real-life, and staff members have suggested that he seems to suffer from depressive episodes. When actress Terri Garr was a guest on Late Night in the '80s and tried to make off-camera conversation with Letterman during a commercial break, he responded by writing a message on his notepad and handing it to her. It read, "I hate myself."