Tonight, David Letterman will leave the late night TV landscape, and as a lifelong fan, I thought I’d do a post about it. We literally grew up on Letterman. My parents were big fans, and I was a born night owl, so, to borrow a phrase from “Parenthood”, I was the only grade school kid who could hum the weird, Hammond keyboard theme to Late Night. In Grade 8, me and my friend David Brown did a disastrous version of our own Letterman show, with David playing Paul, and me playing Dave. We threw the entire gym full of elementary students into chaos when, instead of Dave’s signature canned hams, we started throwing candy into the crowd (without having discussed the plan with any authority figures).

When Dave moved the CBS was probably the peak of my fandom, and I remember feeling the pressure of choosing between his early, revitalized shows at the new network, and the Blue Jays in the World Series that year. Had I known that it would be the last time in my lifetime that the Jays would make it there (so far!) the choice probably would have been easier. And while I watched Dave with less regularity in the past few years (a result of both parenthood curbing my night owl schedule, and Dave’s increased focus on dated political humour, which I didn’t think was a very natural fit) I would still always check in to see who the guest was (making sure to watch if it was Marty Short, or Michael Keaton, or the other hilarious people who always deliver on Dave) and we’d always, always watch his Christmas Eve show.

I’m a bit of a weirdo, because for me, some TV memories are as powerful and memorable as “real” events in my life, and there are a few from Letterman that have stayed with me all these years. Some huge ones have been covered by other media (like the Dick Assman era, or Dave’s inspiring return to TV after 9-11, or his heart surgeries, or even Norm MacDonald’s goodbye last week) but these are the ones that meant something to me, that I saw happen live, and the story behind them.

So in true Letterman fashion, here’s a Top Ten List of the favourite moments I saw, live on Letterman.

10. Brandon Routh’s first appearance on Dave promoting Superman Returns. This is back before Brandon and I became best friends, but it’s a great appearance, and features one of my favourite Dave gags of showing a vintage clip in place of the real clip. Brandon handles himself in a classy way. Watch.

9. Brett Hull does Letterman after scoring his 50 goals for the first time. One of my favourite things that would happen being a fan of Dave is when my worlds collided. Brett Hull was my favourite player since the 1989 season, and hockey was so rarely covered on any network show, my mind was blown to hear in the opener that not only would an NHL player of ANY kind, be on, but it would be my favourite player. He did well, showed that he’s a regular watcher with the GE joke, and did indeed get his 70 goals that year. Watch.

8. Norm MacDonald’s First Appearance. I love Norm MacDonald. But it wasn’t until I saw this appearance on Letterman that I realized how LONG I had loved Norm MacDonald, as, when I was in High School, I used some jokes from THIS appearance in a school project, which got me in trouble with my teacher. I didn’t know the jokes were even his until I saw this appearance a little while ago, and realized that I liked Norm before I knew he was Norm. Watch

7. Sing the Changes. There have been so many amazing musical guests over the years, but a recent memorable one was when Paul McCartney performed with The Firemen. So often our favourite musicians slow down as they get older, and can’t electrify as they once did–it just happens. But this live performance, of a brand new song I’d never heard, but loved immediately, showed me that Paul is in no way slowing down. Plus a Beatle on a rooftop will always be cool. Watch

6. Michael Keaton tells John Popper to “Get out of here”. Unfortunately I don’t have a clip of this, but there was this great, spontaneous exchange one night when John popper was sitting in with Paul and the band (something I loved when he, or David Sandborn would do). Michael Keaton came out as a guest, and John Popper told him that he had created his harmonica pocket vest because he was inspired by Keaton’s utlity belt as Batman. Michael Keaton said “Get out of here!” in response, and Popper replied, “no, it’s true.” Then Keaton, hilariously, said, “No, Get out of here.” sternly. Popper, not missing the opportunity, walked away very sadly and slowly like Charlie Brown. In that moment, I wished I could be on a talk show of some kind, just to be a part of such hilarious spontaneous exchange. I can’t find a clip of it, but here’s a good appearance involving Batman from Michael Keaton: Watch.

5. Paul Molitor Walk-on Speaking of worlds colliding, one of the coolest moments ever was when Dave interviewed Lenny Dykstra from the Philadelphia Phillies, and surprised his audience by bringing out Paul Molitor. We had grown to like Dykstra and the Phillies, despite how hard they played Toronto in the World Series that year, so we were excited to see him on Dave, and have the series even get a mention. But my mind was blown when MVP Molitor walked out, and was funny, charming, and inspiring my fashion for the next five years or so. Watch.

4. Michael Keaton’s short film. I feel a bit bad having two big memories be Michael Keaton (and none being Marty Short, who was equally reliably funny on the show) but in the 80s, Dave had this amazing idea of having celebrities make short films on his show. All the entries are worth a watch (and a few you can find on my YouTube channel) but Keaton’s is the best. Extra points for how hilarious Clint Howard is, as the fish-heads guy. Watch.

3. Bob Dylan sings Jokerman. There’s some contention in my family about whether I really saw this live, given how early this appearance was. But I have a memory (perhaps a false one, but still) of watching this with my Dad. In the years since, Jokerman has become one of my very favourite songs, but the album version isn’t as jaunty and new wave as this great, great performance. I watch this video once a week. Watch

2. Jim Carrey and Lisa Loeb’s first appearance. This is one of my happiest memories, in a weird way, one of those moments where it just seems like everything is going right. I remember this day so distinctly, in the summer after grade nine. Just about every night that summer, me and my pals Jordan and Scott would play baseball until it got dark out, and then walk over to our neighbourhood 7-11. Then I came home, slurpee in hand, and turned on Dave, to find that the funniest guy around (at that time) Jim Carrey was on, as well as my number one crush in those days, Lisa Loeb would be making her Letterman debut. Like everyone else, I adored that song, and as a 14 year old kid, I sure as heck adored the beautiful and talented Lisa Loeb. Unfortunately this clip cuts off, but at the end of the song, when she’s standing with Dave, she did this adorable little cat scratch move on his shoulder (it’s hard to describe). I know it’s dumb, but it felt like she was doing it just for me. And I thought, consciously, man, does it get any better than this? Watch.

1. David Letterman reads my joke live on the air. Back in the early 2000s, Dave’s website would hold a daily contest to write sample jokes for the Top Ten. The site would give you a topic, and you could submit jokes. They were VERY clear that once you submitted it, they owned the joke, but you had a shot at winning a t-shirt. Every day, for months, I would submit jokes, and none would ever be chosen for the website. Then, one day, there was a topic, and I was in a bit of a dry spell, so I submitted the only joke I could come up with, and hit send. And of course, that’s the one they chose. So it appeared on the website top ten, and I was sent my Late Show Online t-shirt.

But the story doesn’t end there. A few weeks after I got my shirt, I was watching Dave, and the same topic came up. And then, at number two on the list, he read MY JOKE. Now, the trouble is, the joke was pretty dated, and not that funny, so when I tell people about it, it never, ever gets a laugh. But the topic was “Top Ten Ways Californians Are Conserving Energy” and if you ever come across it online (I cannot find it, myself) I will tell you which joke is mine. Hint: it involves Kate Hudson. Happy hunting!

That’s it! Thanks, Dave, for a lifetime of humour and great TV moments. There will never be another Letterman.

Thanks for reading, I love you.