America’s Fool
Thank you Stephen for 20 glorious years…
It was the fall of 2006 as I wandered downstairs from my dorm room. Somebody had the Daily Show on, and as Jon Stewart signed off, it transitioned to the next show. A scream erupted from the TV, like a bird was screeching…
Was that a bald eagle?
Enter Stephen Colbert: running around his stage like a rockstar, audience on their feet, sending their adulation.
He strutted out in a Brooks Brothers suit, a signature Bic pen in hand, and eyebrows of justice.
He may have started on TV as the Robin to Jon Stewart’s Batman, but his talent was so obvious that he wouldn’t be without his own show for very long.
From 2006 to 2015, Stephen inhabited a character that was a masterclass in the art of satire: a Fox News type guy, making fun of the those in power. His humor was savvy, like he was in on the joke, but his character didn’t seem to know it. He was so good that both Right and Left thought he was one of their own.
On the Colbert Report, Stephen embodied the Shakespearean archetype of the fool: the ignorant knave that somehow speaks the deepest truths to the most powerful people. He was so good at his craft that Nancy Pelosi and other Democrat leaders banned their party members from doing interviews with him because he made them look ridiculous.
This gift came at a great cost — his humor was forged in a crucible. As a young boy, he lost his father and two older brothers in a plane crash. Somehow through that pain, he learned to alchemize the human experience, to turn sadness into joy.
As he transitioned from cable to mainstream TV and started on the the Late Show, he let go of the character schtick and decided to play the hardest role of all—himself. In the Trump and Covid years, we needed his true self even more than we knew at the time, because we needed an alchemy that could only come from the depth of his soul. He bore witness that what we were seeing was in fact crazy, and we weren’t the crazy ones.
His show is scheduled to end this May. Here is a tribute to the past 20 years…
*NOTE* Almost all the video clips are time stamped, so most will cut to the best part. Don’t be afraid to click and see his talent…
His Rarity
Most celebrities are a one-note kind of talent. They can sing, act, or be funny. Few can do more than one. Even less can do more than one well.
Stephen is multidimensional. There are no public performers today with his breadth of talent.
His memory is incredible:
Look at his recall in a recent interview with Michael Pollan. He could full passages from memory:
His witticism:
Unfortunately, most of the old Colbert Report clips are gone, so I can’t link any (you gotta trust my memory here), but in so many of his amazing interviews, he showed one of the fastest minds around.
If he was debating an opponent and they straight up disagreed with his position, regardless, he would still say “I accept your apology.” It was always hilarious because they weren’t apologizing at all and it short-circuited their brain. (It’s a fun trick to do with friends actually, try it :)
He’d do live shows, late into his career:
After a major political event, he would do a live show. It was fresher and hit harder. He and his crew would only have 1-2 hours to hours to get jokes lined up. Even with a full cast of writers, that’s impressive. With his improv chops and strong writing process, you could hardly tell the difference.
He can sing:
He actually had a voice! He could hang with broadway performers like Anna Kendrick here:
Or watch him sing a cover of Friday (lower register but still impressive).
He has ballz:
In countless moments, he said the craziest and most awkward thing to the person in charge, and none was as bold as his speech at the the White House Correspondents Dinner to George W. Bush. How many comedians would have whiffed this because it was the president…but not Colbert.
Top Moments
That time he lost an award to Barry Manilow. This is a classic from the Colbert Report Era:
In a sketch on the Report about Koalas suffering from Chlamydia, he famously asked “whoever is fucking our koala bears, KNOCK IT OFF!”
After his mother passed away, he gave the most moving tribute and said losing her was like “the enormity of the room whose door has now quietly shut:”
Truthiness—he foreshadowed where politics was headed. Not based on reality but in our feelings. It became a recognized word by Merriam-Webster because…it hit a nerve.
He foresaw MAGA: His book Re-Becoming the Greatness We Never Weren’t was MAGA before there was even a MAGA…
One of his Report guests came on to advocate for ending marriage as an institution, and after letting him ramble for few minutes, Stephen ends the interview by asking “but what if this is just an elaborate way for you to be an asshole?”
Colbertisms: “Great president OR the GREATEST President?” He would ask a question and only give “great” or “greatest” as the two options.
Here is a classic Colbert Interview segment from the Report days (also…this was filmed before 2010, not in 2026 like it feels)
His satire was unparalleled. Look at this clip of his actual testimony before Congress — “This is America. I don’t want a tomato picked by a Mexican. I want it picked by an American, then sliced by a Guatemalan and served by a Venezuelan, in a spa where a Chilean gives me a Brazilian.”
Even though he played a character, when people treated him as a real person, his true self couldn’t help but peak through. Listen to why he cared so much about immigrant laborers (the schtick had deep roots):
His “Better Know a District” from the Report was LEGENDARY. This was the best full clip I could find (c’mon Paramount Plus!) but even it was amazing:
When Daft Punk broke their promise to come on his show, what did he do? He made his own music video to mock them. He’s that talented and he’s THAT petty (the whole clip is a procession of celebrities):
Helping Anderson Cooper grieve: Notice how he so casually quotes the Lord of the Rings like some quote sacred texts. And watch him help his friend get through a dark time…
“What punishments of God are not gifts?”
“It’s a gift to exist. And with existence comes suffering. There’s no escaping that.”
One of his top interviews on the Late Show was Will Ferrell. This entire clip is worth the watch, even it’s more about Will here…but it’s amazing…
Remember that time that Nicki Minaj made Stephen blush because she made a rap lyric on the spot about wanting to…get with Stephen? Ya, it was an instant classic for a reason:
“Can I get you some duct tape?” That time Stephen brought on an instagram influencer who couldn’t stop pulling up her dress. Nobody could just say the awkward like this man could:
“You go to hell:” Stephen learning how to pronounce Irish words with Saoirse Ronan:
If you know anything about him, you’ll know he’s the biggest Lord of the Rings fan on earth. That’s not an overstatement either. He beat an on-staff expert for the LOTR movies in a quiz off. He quotes the books like some people quote sacred texts. In honor of the movies, he made one of the best LOTR tributes with almost all of the original cast. Epic, just epic:
Thank You, Stephen…
For the past twenty years, I’ve watched you (I was 19 when I first watched you, and I’m about to hit my 39 birthday this June). My adult years have been punctuated by your performances: You started the Colbert Report right as I started college. You started the Late Show as I got married. And as the strange phenomenon of the Trump presidency kicked off, you were there to give voice that we were seeing what we thought we were seeing.
Through rough times in my life, I’ve always had you to look forward to at night. You made my days and my life easier, making the strangeness of the past decade far more bearable. It’s like you filtered the poison before it reached me. I didn’t realize how much I needed you until you were about to be taken from us.
I saw you grieve the loss of your mother and will never forget the line “enormity of the room whose door is now shut.” I grieved with you. And it brings tears to my eyes because another door is about to close. I’m sure you’ll back but in a different capacity (podcast, Netflix?) and I’ll follow you there too…but I’m not ready for this room to be closed.
I wished I was able to see your show in NYC before it ends. But you’re so loved, it seems like it’s impossible to get in because we all want to say goodbye. If I never get to tell you thank you with my presence, I hope this post can at least do the same. I am so grateful for you.
I don’t know you personally, but I know you. I wish you and Evie all the best. I know saying goodbye will be one of the hardest things for you, and I hope it can still be a lovely experience. But I’m grateful for you. I’m glad you had the time to see it was coming. I wish you the best.
I don’t know what you’ll be doing after, but I will still follow you. Who else will alchemize our collective pain for us? We still need you Stephen.
And I almost missed it until I was assembling this: when you were asked who’d you love to interview from Lord of the Rings, you mention Neinna, Gandalf’s patron, and said “she weeps forever and turns grief into wisdom.”
Thank you for turning your grief into our wisdom.
I’m so glad we “better knew you.”
