During the final two weeks of Late Night With Conan O'Brien, Conan and his staff sorted through sixteen years of timeless, classic moments, to generate the Late Night Top 10 Moments list, as selected by staff, viewers, and Conan O'Brien himself. They are: Following The Tonight Show on the eve of the Friends series finale, Conan had quite the show ahead, featuring Hollywood star (and husband of Friends star Jennifer Aniston) Brad Pitt lined up, as well as a musical performance from Janet Jackson. So how to top them? By featuring the most luxurious automobiles on the market...next to his "Green Machine," a 1992 Ford Escort SHO. Conan, determined to sell his car to the highest bidder, so he could purchase a "large estate" somewhere in Western Europe, heads to both the Cooper Classics Collection and Christie's auction house to have the car appraised alongside Ferraris, Lamborghinis and Porsches. After failing to find a buyer "to his liking," Conan ends up giving the car away to Pitt at the end of the show. In San Francisco for a week of shows, Conan decided to sample some of the best the famed Napa Valley had to offer, heading up north to the Spring Mountain Vineyard to sample the finest wines in the region. Finding no struggle in drinking at 8:30 in the morning, Conan headed around the vineyard in a decomissioned Swiss tank, serenaded the staff with a guitar solo in the winery cave, made inappropriate sexual innuendos in regards to the wine shaft being inserted into barrel holes, and attended a tasting dressed to the nines (complete with smoker's jacket and pipe). Conan then concluded his morning with an oversized novelty wine glass, stumbling through the vineyard while trying to top off his bottle. Deciding to take in the beautiful fall foliage of New York state, Conan decides to take a camera crew to go apple picking with a friend...A-Teamer and perennial Conan favourite, Mr. T. After having difficulty finding quality apples, Mr. T decides to take it upon himself to blame nature instead, elbowing bad apples, berating mealy ones, and actually verbally abusing trees producing bad fruit. Taking in the beautiful weather and atmosphere, Conan and T decide to exhcange poetry quips next, revealing perhaps the most hilarious laugh in TV history from Mr. T. Finally, Conan and T join a group of tourists on a hay ride through the orchard, where Conan and Mr. T sing to the crowd, before T is nearly knocked off of the trailer by an errant branch. Perplexed by why Late Night does not air in Houston until 2:40 A.M., Conan heads to the Lone Star State to see who is watching when his show comes on. Driving through the empty city streets at 12:30, when his show airs everywhere else in America, Conan decides to prep the city by visiting those who will still be awake to watch at 2:40, including a bail bond office, an emergency room, a convenience store, and a dorm room at Rice University. Conan finally heads to the Houston bus station, where he is confronted by a bewildered (and most certainly high) biker only known as "Buffalo," who Conan narrowly escapes with his life from. Conan ends his time in Houston at the Astrodome, where at the conclusion of Late Night is seen fast asleep, alone in the empty stadium. Trying to capitalize on the success of massive boy bands like Backstreet Boys, *NSYNC and 98 Degrees, Conan recruits five young hopefuls to create and manage his own boy band, which he aptly titles "Dudez-A-Plenti." Demoralizing his singers step by step, Conan changes all of their names, their poses and dance moves (even having one member wear a vanity respirator, to one up the vanity cane used by A.J. MacLean), makes them write ridiculous song lyrics, and has them create a horrendous music video. Finally, Conan debuts the Dudez to the world on Late Night, having the band perform "Baby, I Wish You Were My Baby" for America. After discovering the comic potential of Late Night associate producer Jordan Schlansky almost by accident during the WGA Strike, Conan decides to head out on the town with Jordan for more comic gold, heading to Jordan's favourite Upper East Side Italian restaurant. Downing evidently far too much wine early on, Conan proceeds to interrupt every one of Jordan's travel story with the ending "...then you were raped!", much to the chagrin of Schlansky. Conan then lets loose on the eccentric, yet pompous, Schlansky, shouting death threats his way every time he uses long-winded metaphors simply to describe food or a picture. The odd couple finishes the dinner by exchanging Led Zeppelin lyrics, and then heading off on Jordan's Vespa to a "German disco" on the Lower East Side. Deciding to take in a new hobby for the spring, Conan wakes up bright and early and heads to Central Park, to join a veteran bird watching group and learn the essentials behind "birding". Struggling to learn technical terms, and avoid repeats of birds already seen, Conan tries devising a hand-signal code amongst the birders, which fails miserably. Conan's group then meets up with other "rival" groups, and in an attempt to throw them off, Conan scales a tree in the park, with an owl puppet handy, and begins calling from the trees, throwing off birders and pedestrians alike at the odd calls (and very well-spoken English for a bird). Conan then finishes off the morning with a "day-cap," revealing his binoculars to really be a hidden flask, which he splits with the birder group. The only Top 10 highlight not to feature Conan, this all-time Triumph The Insult Comic Dog classic took his insults and slurs to new heights, as Triumph hit the Zeigfeld Theater for the New York premiere of Star Wars: Episode II. Slamming nerds left, right and centre, Triumph shone the light on the lone female in the crowd, a pregnant reveller, and a young Darth Vader. Tensions arose when a Lord Of The Rings fan crashed the party (and went one-on-one with Triumph), and then when the crowd was really "asking to get pooped on," Triumph brought in the greatest ammo of all: a Spock-clad Star Trek fan, flipping the bird to the Jedi faithful. After discovering the popularity of Late Night in Finland (due in particular to the booming popularity of Conan, who bore a resemblance to Finnish President Tarja Halonen), Conan decided to pack his bags and bring Late Night to Finland in the dark of Scandanavian winter. After parttaking in a traditional nude spa, a sled ride at the edge of the Arctic circle, an appearance on Finnish late night TV, and wandering the streets of Helsinki, to personally reply to letters he had received back in America (including one hilarious bit in trying to track down a man named "Fagerstrom"). Finally, Conan got the chance to meet the woman he helped propel to power at the Presidential Palace in Helsinki. The #1 moment, the moment which Conan O'Brien himself declared his favourite, and hopes to have played at his funeral. Conan visits the Old Bethpage Historical Restoration society in Bethpage, NY, to observe, and then play, a game of baseball...played under 1864 rules. While first learning the rules of the game from the referee and spectators, Conan makes passes at the ladies observing the game, even trying to convince one her faux-husband, away fighting in the Civil War, chickened out of battle and was seen "making out with a dude." Conan then suited up in full 1864 gear and took to the field, shouting 1864-era obscenities at opposing players, arguing with the referee, and even charging the mound to dispute a foul ball. Finally, Conan shocks the whole village by discovering "demonry in the sky!" (i.e. an airplane), adding the final major culture shock to his already wild presence in the quaint world of 1864 America.