The Tonight Show with Jay Leno (1992-2009)

Here are six of the luckiest guys in the world: Steve Allen, Jack Parr, Johnny Carson, Jay Leno, Conan O'Brien, and Jimmy Fallon. They’ve all hosted the king of late night, seminal talk show The Tonight Show. But it’s not because of that coveted real estate in beautiful downtown Burbank (though the show originated in New York City) that viewers should be envious, but rather because some of the hottest asses ever squeezed into tight pants or a miniskirt have been sandwiched between the host and co-host. While no actress has yet to strip down on the air, they’ve all exposed their breast bits for the camera. And where else can you hear Hugh Grant talk about getting a hooker to blow him? There have been other hosts, but if you're a millennial, the man you'll always associate with The Tonight Show is the car obsessed, big chinned boy from Beantown, Jay Leno. We won't get into all the drama that saw Jay take over for Johnny, much to the fury of the assumed heir to the gig, David Letterman, nor will we recap the issues Jay had with Conan O'Brien when he retired, then unretired from the show. Instead, we'll simply applaud the man who delighted millions with his small-town news segment "Headlines," his oft ripped off man on the street interviews segment "Jaywalking" and the hidden camera segment that really made Howie Mandel a star, "Howie Do It." But what really had viewers tuning into NBC from 1992 to 2009, and then again from 2010 to 2014 was all the hotties Jay brought out for late night viewers to dream of all night. From a cleavage baring Paula Abdul and Tyra Banks, to a near upskirt shot of Gisele Bundchen, The Tonight Show was always a "will they slip a nip, they just might" show. To that end, Cameron Diaz once wore a dress so nippy the Peacock network might as well have called itself the grab your cock network, while Janet Jackson showed a bit of crack as her original "wardrobe malfunction." We could spend all day talking about the hotties that showed their stuff on The Tonight Show with Jay Leno. If only they'd been allowed to get naked as a jaybird!