A Sunday Funny:

Why Does An Extremely Ill-Timed Gift Basket Make Me Laugh?

Another in an occasional series on things that never fail to crack me up, for reasons I can never fully explain

Of the supposed fundamental pillars of proper comedy, one of the most sacred is “timing.”

Get to the punchline too quick?

You’re toast. You’ve missed the moment entirely.

Hit your mark too late?

No good, son. You just slipped-up on your set-up.

It’s a surprisingly difficult thing to pull off.

The rhythm has to be just right, with your perfectly pregnant pauses precisely pitched to perfection. My cheesy alliteration aside, it’s a fact: timing is essential to the construct of a great joke.

But what if we’re talking about timing in a broader sense?

Such as… simply arriving someplace when you were supposed to?

Here’s a prime example of – wait for it – painfully poor punctuality. Proving that in extreme cases, perfect comedy can spring from spectacularly bad judgment.

Such was the case on January 19, 2010, during what would be one of the final episodes of The Tonight Show With Conan O’Brien.

As NBC was unashamedly dumping Conan as the show’s host in favor of a returning Jay Leno, the Peacock Network late-night lineup entered a brief period of “creative reshuffling.” A few careers took a hit, loyalties were complicated, and the future of late night talk show comedy became a matter of network and contractual logistics.

Through it all, Conan handled his exit with quiet dignity and sharp wit, a reminder that grace under pressure can be its own kind of legacy.

Still, to be dumped in front of 20 million people? I can’t imagine the humiliation and demoralization.

The stars who came to visit and sit on the couch while chatting with Conan tried, under the circumstances, to be kind and empathetic. But as the final week’s celebrities were behaving with cordial and respectful platitudes, one guest went in a completely different direction:

Comedian Norm MacDonald.

The Surprise Walk-On is a corny yet venerable show business tradition.

Primarily a talk show device the, “Hey, can you believe who just stopped by?” guest appearance has been a staple of late-night programming.

Rarely a truly spontaneous event, it’s most often just scripted theater, designed to make the show seem loose, hip, and playful.

The fake surprise has become so common that audiences have developed a sixth sense for it. We can usually tell when an “omigod it’s them” drive-by guest spot is contrived.

The host’s mouth is a little too agape, and the whole thing feels just a bit too “smooth.”

The real magic happens in those rare moments when the host seems genuinely caught off guard; not by the faux visit, but by what the guest has up their sleeve.

While Conan was almost certainly aware that MacDonald was going to show up, his reaction to the bit itself suggested that he had no idea exactly what was coming.

This was “Norm comedy” at its finest.

His stand-up and guest appearances always teetered on the edge of chaos, as if he might veer off script at any moment and take everyone with him.

Which he usually did.

The gift basket bit had all the hallmarks of classic MacDonald.

On the surface, it was simple: a slightly befuddled guy showing up really late with a gift. But underneath, it was a clever lesson in how to get a laugh while subtly addressing the elephant in the room.

MacDonald’s delivery was what elevated it from clever to brilliant:

• He didn’t wink at the camera or oversell the joke.
• He played it completely straight, as if he genuinely had just remembered to come by and visit.
• What some mistook as a little shot at Conan? In reality, it was a guided missile, but with “the NBC brain trust” in the crosshairs.

So: What’s So Funny About It?

Why does this two-minute fake walk-on make me laugh? I think it’s few things at once:

– I love the singularity of the moment.

A bit that could only happen once, under exactly those circumstances. It’s a one-and-done joke that could never be repurposed for another time.

It was as clever as it was unique.

– It’s the host’s and crowd’s collective reaction.

Conan’s head drop, along with the audience’s transition from cringing to laughter is a delight.

And: if you look beneath the surface, it also showed a quiet kind of loyalty.

The kind we’d all hope for in a friend.

As we all know, comedy is subjective. But this kills me. See if you agree.

It wasn’t a joke at NBC’s expense. And certainly not at Conan’s. It was a weird, brilliant act of solidarity.

Late? Technically, yes. But also precisely on time.