The show opened with a daring stunt in which Conan dives into the Hudson river (and if it's true what they say about NYC, that takes a lot of guts!). Then O'Brien delivered his 'Conologue' not from the usual set, but a redecorated studio 8H (SNL's home base). Perennial talk show guest Tony Randall teamed up with Pimpbot 5000 to introduce a montage of great guests and Tom Arnold was teamed with Triumph the Insult comic dog to present a collection of clips featuring Conan & Andy all over the world. Back then Triumph didn't even have a body, just a rubber face, though it's inspired to see Arnold coming down the Award style steps with an actual Hungarian mountain dog on a leash. Robert Smigel not only voices Triumph, but also President Bill Clinton in 'clutch' mode (i.e. lips superimposed on a picture). The commander in chief introduces a Clutch clips package of various people (almost all voiced by Smigel). Also, Chris Rock and Lisa Kudrow share some brief pre-recorded 'Favorite Conan Moments' and Conan gets a little surprise from Adam Sandler.
Still, compared to the three year anniversary from 1996, this show does seem a bit less inspired. There were much more C-status celebrities in attendance two years earlier, appearances by both Letterman and Leno, a desk ride by Conan and Andy (this time around they watch some new cable channels instead) and a segment on 'lovely violence' introduced by Carl 'Oldie'Olsen (William Preston), who passed away in early 1998. It's also a bit weird to see an advert for a 'Too hot for Late Night 5th Anniversary video with 3 diff collectible video covers' that's basically the show we're watching right now. That's right, folks a mere ten years ago video's were all the rage and most people had no idea what a DVD was.
8 out of 10
PS. Here is a personal top 5 comedy bits from the first five years of Late Night that unfortunately weren't in either special: 5 - The three remaining Beatles (in Clutch form) present a song based on a recently discovered John Lennon recording (his answering machine message). 4 - Babe the cute little piglet uttering "You big Krunkhole" (a swearword so new the censors didn't pick up on it yet) 3- Clutch Johnny Cochran's unused rhymes in the O.J. Simpson defense ("He was # 32, so no crime could he do". "He was in Naked Gun, how could he be the one?"). 2 - Some Adult film stars proving their acting prowess by recreating the signing of the declaration of independence (with hilarious money shot stills to introduce each of them). 1- Foam rubber Conan & Andy (one resembling Howdy Doody, the other a blond boy with the body of a Care Bear) at the Repubulican convention (ending up with Foam rubber Andy vomiting in their hotel bathroom).