Conan O'Brien's partying like it's 1999, but is his Late Night talk show ready for Y2K?

By Bruce Fretts
Updated November 05, 1999 at 05:00 AM EST

Dear Conan O’Brien,

First of all, congrats. After your famously rocky 1993 launch, I was one of the many TV critics who never thought you’d still be hosting Late Night (NBC, weeknights, 12:35-1:35 a.m.) in the year 1994, much less In the Year 2000…. Hey, that’s the title of your new book, based on the popular bit in which you and sidekick Andy Richter peek into the future (sadly, one prediction has already proven incorrect: ”Elizabeth Dole will be elected President, making Bob Dole America’s First Man — something already verified by fossil records”).

I’m sure you’re feeling more confident these days, as well you should. NBC is sending you on your first road trip to L.A. Nov. 9-12, and you’ve lined up such big-name guests as Arnold Schwarzenegger, Jennifer Love Hewitt, and Ben Affleck. You’ve held your ratings against Craig Kilborn, the demographically competitive new host of CBS’ Late Late Show. Yes, 1999 has been a very good year. But let me ask you this: Have you given any thought to what Late Night will look like In the Year 2000…?

As a matter of fact, there are big changes ahead for you. You’ll be losing two of your most reliable comic foils: Richter, who’ll be leaving in May to pursue an acting career, and Bill Clinton, who’s provided many a punchline in your monologues and skits. Allow me to offer some free advice on how to handle these imminent departures.

You’ve said that you’re not going to hire a new sidekick right away out of respect for Richter. Perhaps you should reconsider that. Kilborn’s working solo — the guy even serves as his own announcer — and there are nights when he looks awfully lonely out there. You could use bandleader Max Weinberg, who’ll be back from playing drums on Bruce Springsteen’s tour, but let’s face it: In the snappy-comeback department, Weinberg is no Paul Shaffer.

While searching for a new sidekick, here’s a good guideline: Think outside of the Ed McMahon/Andy Richter box. We’ve come to expect a pudgy white guy on the couch, but it’s time to shake up that perception. How about Nipsey Russell? The quick-witted game-show panelist/poet always kills when you use him in sketches. Or why not bring a woman to the after-hours boys’ club? Janeane Garofalo might need a steady gig after Mystery Men‘s recent box office nosedive.

Now, on to the presidential question. The best-case comedic scenario for a Clinton successor was eliminated when Dan Quayle dropped out of the race. Republican front-runner George W. Bush offers limited satirical potential (how much longer can you do coke jokes?). Democratic rivals Bill Bradley and Al Gore? Dull and duller.

That’s why you’ve got to do everything in your power to elect Donald Trump. The guy’s a comedy gold mine. You’ve got the skirt-chasing angle (just recycle some of your old Clinton material and insert the name ”Trump”). You’ve got the bizarro blow-dried hair. And those permanently puckered lips lend themselves perfectly to your fake newsmaker interviews.

With Nipsey by your side and The Donald in the White House, you’ll enter the new millennium laughing. Oh, and one other thing: You might want to change the name of that bit to “In the Year 2010….”

Your Late Night pal, Bruce