32. The Late Show With David Letterman - (1993) - 19 points (1 of 9 lists. Highest ranking - #7 Minnesota)http://www.imdb.com/title/tt0106053/The Late Show with David Letterman is a multiple Emmy Award-winning hour-long weeknight comedy talk show broadcast from the Ed Sullivan Theater on Broadway in New York City. The Late Show is well known for its repeated absurdist segments, often taking the form of competitions or audience participation. The charm of these segments is often that they are completely pointless, yet are taken seriously by Letterman and all involved. Currently, the show's regularly scheduled segments consist of "Small Town News" on Mondays (coincidentally and possibly competing with Leno's similar segment, "Headlines") and "Fun Facts" on Fridays. Thursdays often feature a rotating set of three audience participation segments: "Know Your Current Events," "Stump the Band," and "Audience Show and Tell."
Every Halloween, Letterman stands in a house-like set on stage, where he answers a door and greets a series of trick-or-treaters dressed in elaborate, humorous costumes (a recent example being a gas station sign with changeable prices). The children are then given "treats" which have consisted of unusual items such as Lipitor, useless Yankees World Series tickets, and a Tonight Show tote bag. Every Thanksgiving, Letterman visits his mother at her Indiana home via satellite, and tries to guess the two pies she has baked for her family dinner. Letterman will also show footage of that year's company Thanksgiving party, which often includes a particular clip from a previous party in which Letterman serves food while dressed in a pilgrim costume. For Christmas, Letterman will often dedicate a segment to toy expert Shannon Ice, who demonstrates many of the newer toys that will be available during the upcoming season. The main appeal of the segment is Letterman's tendency to engage in horseplay with the various toys on display.
In a 1995 Late Show episode, as a birthday present, actress Drew Barrymore stood on Letterman's desk and flashed her breasts, as part of an erotic dance. (The cameras only showed her from the back, during the flash). The dance shocked the usually unflappable Letterman; it was reportedly a gift from Barrymore, for his birthday. Letterman later said, 'I couldn't have been more pleased.' A later skit on The Late Show entitled "The David Letterman Story" referenced the incident where Letterman claimed his most memorable and favorite moment on the show was "when Drew Barrymore got on the desk and took her shirt off."
No, Conan O'Brien is not on the list for some reason. But, hey, neither is Jay Leno.