6. Conan Goes to Trucking School (1997)
If at any point during the past 25 years, Conan O’Brien wanted to walk away from comedy he would have plenty of skills to fall back on for a new career. One of those would be trucking thanks to the class he took in 1997.
It may be easy to imagine a late night host today doing something like this. Jimmy Kimmel or James Corden come to mind but there wasn’t anyone else in late night wearing a cutoff shirt and jumping out of 18-wheelers in 1997. So much of what we enjoy about late night in 2018 is because of what Conan O’Brien was doing at the start of Late Night.
With “Trucking School” we go back to seeing Conan primarily making himself the joke. An easy path would be to identify an unusual or strange job and have Conan find out more. Instead, he’s using a normal job no one would think could be the mined for comedy. But he delivers by opening himself up as the point of ridicule. Still, there is that hint of the over-confident idiot that Conan can play so well, making this clip a highlight of his full range.