The talking heads of late-night television rake in oodles of money for their nightly hijinx and some of them aren't shy about showing it off. Yeah, we're looking at you and your 100 cars, Jay Leno. Leno's fellow nocturnal comedians might not splash out on a gaggle of flashy rides—or set up a web site for their garage—but they sure invest in some palatial pads. Late night small-fry and SNL-alum Jimmy Fallon might be the new kid on the block, but he's well entrenched at this 1883 co-op overlooking NYC's private Gramercy Park above. In 2006, Fallon was thinking about moving out and put his two seventh-floor units on the market for $3.75M. In 2010, he changed his mind completely and bought another $1.35M apartment on the eighth floor of NYC's oldest cooperative. Guess he had no time for a house hunt once he got the seat behind the Late Night desk.
? So where's this Jay Leno character bedding down? This Los Angeles compound, comprising two sizable estates in tony Bel Air, is what Leno calls home—though those precious cars live elsewhere. Leno purchased the uphill house, a 3,400-square-foot five-bedroom number, in 1987 and added the downhill property 10 years later, maybe just for the pool.
? Leno's main ratings rival, David Letterman, has settled on the other side of the country, in New York's Westchester County. Letterman also maintains a ranch in the Tetons, but spends most of his time at this 102-acre estate in North Salem, N.Y. The shingle-style spread is certainly impressive, but less so is the office park it calls a neighbor. He's lived here since 2001, and only added to his acreage since moving in.
? Leno may have unfairly snatched his show back after handing it over to Conan O'Brien, but O'Brien will have a hard time registering serious complaints from the comfort of this L.A. pad. The TBS employee scooped up this Brentwood, Calif. six-bedroom for around $10M in early 2008, and later hosted an especially lighthearted interview with 60 Minutes during the intra-network showdown.
? Though he wasn't embroiled in any hiring or firing scandals in recent memory, former Ben Stein sidekick-made-good Jimmy Kimmel still has plenty of cash on hand for his real estate whims. In 2008, Kimmel laid down more than $6M for this L.A. estate boasting 5,500 square feet, five bedrooms, five baths, and a partially covered swimming pool.
? Jon Stewart, the irreverent outsider compared to the network heavyweights, made a big-time purchase in 2005 at Tribeca's 161 Hudson Street in NYC. For $5.8M, Stewart secured a 6,000-square-foot penthouse with a terrace and a private roof deck. The apartment was previously home to more than 1,000 pet turtles, so we'd imagine some remodeling was necessary to bring it up to celeb standards.
· Jay Leno's Garage [official site]
· 34 Gramercy Park East #8BF [Streeteasy]
· 34 Gramercy Park East #7BR [Streeteasy]
· Jay Leno's House [Virtual Globetrotting]
· David Letterman's House [Virtual Globetrotting]
· Conan O'Brien's House in Brentwood [Hooked on Houses]
· Real Estate: Jimmy Kimmel / Beverly D'Angelo [WizBangPop]
· House of Stewart [Forbes]