My Life as Preparation H Raymond on ‘Late Night with Conan O’Brien’

Meet the World’s Most Helpful Hemorrhoid Hero

Long before prestige TV and streaming wars, late-night talk shows were where the truly weird ideas went to live.
On Late Night with Conan O’Brien, you didn’t just get celebrity interviews and monologue jokes you got a parade of deeply unhinged characters: a bear with terrible habits, ducks with even worse habits, and a whole lineup of sketch oddballs who looked like they escaped from a fever dream at Rockefeller Center.

And then there was Preparation H Raymond a big-eared, relentlessly upbeat man whose entire mission was to walk down the aisles and lovingly hand tubes of hemorrhoid cream to strangers.
No capes, no superpowers, just the determination to keep America’s butts slightly less miserable.
On Cracked.com, writer Brian VanHooker later chronicled that life in a now-beloved feature, reflecting on what it meant to be the human embodiment of a pharmacy aisle punchline.

This is the story behind that character how he fits into Conan’s bizarre late-night universe, why the joke worked so well, and what “living” as Preparation H Raymond tells you about comedy, embarrassment, and audience joy.

Late Night with Conan O’Brien: The Golden Age of Unhinged TV

To understand Preparation H Raymond, you have to understand the ecosystem that created him.
Late Night with Conan O’Brien was famous for sketches that were proudly too weird for primetime: the Masturbating Bear, the FedEx Pope, Pierre Bernard’s Recliner of Rage, Queen Elizabeth calling in with petty complaints, and an endless parade of surreal “New Characters.”

The show’s writers and performers leaned hard into absurdity. They didn’t just flirt with bad taste they took it out for drinks, gave it a fake ID, and sent it dancing through the studio.
In that world, a character whose sole purpose was to distribute hemorrhoid ointment to a cheering crowd made perfect sense. The more specific and strange the joke, the more it felt like classic Conan.

Late-night audiences back then weren’t just watching; they were part of the experiment. If a bit died, Conan would gleefully point out how badly it was bombing.
If a bit killed like a guy in a suit with massive ears handing out butt cream it could become a recurring superstar.

The Birth of Preparation H Raymond

According to fan archives and the Conan O’Brien Wiki, Preparation H Raymond debuted on January 3, 2001, in a segment literally called “New Characters for 2001.”
Played by long-time writer and performer Brian McCann, Raymond was designed as a Johnny Appleseed–style figure whose life’s calling was to bring medical relief directly to the people whether they asked for it or not.

Visually, the character was instantly ridiculous: big, slightly royal-looking ears, an almost regal posture, and the energy of someone who believed, deep in his soul, that tonight’s gift of hemorrhoid cream might actually change your life.
The bit quickly evolved into Raymond striding confidently through the aisles, handing out tubes of Preparation H while a theme song proclaimed that “Raymond’s here to help,” usually tied to whatever current events the writers wanted to mock that week.

Over the years, Raymond popped up for holidays, special events, and random episodes: Thanksgiving warnings about “five nights of rectal hell,” Christmas visits loaded with “cheer and cream,” and even a trip to Toronto as the world’s least subtle health ambassador.

Suiting Up: Inside the Life of a Late-Night Character

Being Preparation H Raymond wasn’t just about slipping on some prosthetic ears and winging it.
Late-night characters rely on precision: timing, body language, how long to linger in a row, when to ad-lib, and when to let the audience’s laughter do the work.
Shows like Conan’s often pulled double duty from writers, who not only created the bits but also performed them live, night after night, under hot studio lights.

Imagine the preparation process:

• An over-caffeinated writer’s room pitches something like “hemorrhoid cream hero.”
• Some poor producer has to arrange an unholy number of tubes of Preparation H.
• Wardrobe and makeup collaborate to answer the question: “How big can his ears be before NBC standards calls?”
• Meanwhile, McCann memorizes his lines and beats plus backup jokes in case someone in Row 3 becomes the accidental star of the bit.

Because the sketch required direct audience interaction, Raymond couldn’t just hide behind the desk or stay on stage.
He had to break the invisible barrier between show and studio, looking people in the eye while handing them a product nobody really wants to talk about out loud.
That collision public embarrassment plus cheerful generosity is exactly where the comedy lives.

Why Free Hemorrhoid Cream Is Comedy Gold

There’s a simple late-night truth: give the studio audience something for free, and they will love you.
It doesn’t really matter what it is T-shirt cannon, keychain, random energy drink people will react like they’ve just won a small lottery.
In the case of Preparation H Raymond, you had a perfect storm: free stuff, live TV, and the most giggle-inducing medical product on the shelf.

The joke worked on multiple levels:

• Taboo topic: Hemorrhoids are exactly the kind of bodily misery no one brags about, especially not in public. Making them the center of a celebratory bit is funny because it breaks that taboo.
• Earnest delivery: Raymond isn’t grossed out; he’s thrilled to help. The straighter he plays it, the funnier it becomes.
• Audience complicity: Each person taking a tube is silently admitting, “I might need this someday,” while the crowd laughs at that unspoken confession.
• Visual absurdity: A man with royal ears, handing out ointment with a proud grin, feels like a cartoon wandering into real life.

Late-night characters live or die on clarity.
You don’t need a long backstory. In three seconds, you know who Preparation H Raymond is and what he wants.
That clarity is why he could keep returning for years without needing a single “previously on” recap.

Between the Laughs: The Real Work Behind the Bit

One thing Cracked pieces often point out and that applies perfectly here is that comedy that looks loose and chaotic is usually sharply crafted behind the scenes.

Every Preparation H Raymond appearance had to be slotted into a precise show rundown.
Producers had to consider camera angles, aisles to walk down, how long the bit would run before Conan had to cut to commercial, and how to keep things safe while a man in costume is weaving through rows of people, arms full of giveaway tubes.

Meanwhile, McCann had to keep Raymond locked in:

• Stay in character even when someone says something unexpected.
• Keep the energy high enough to read on camera, but not so manic that it derails the entire episode.
• Land the jokes that tie the ointment to whatever topical thing the show was skewering that night baseball steroids, Thanksgiving overeating, Christmas indulgence, you name it.

That’s the invisible part of “my life as Preparation H Raymond”: the hours of writing and rehearsal that happen so the audience gets three minutes of effortless, joyful chaos.

Fan Culture and the Afterlife of Preparation H Raymond

Like a lot of Conan’s recurring bits, Preparation H Raymond took on a second life online.
Old clips of Raymond visiting Toronto, returning in 2001 and 2002, and handing out Christmas-themed cream are archived on YouTube and fan sites, letting a new generation discover the character’s deeply weird charm.

On Reddit, fans regularly bring him up as an underrated GOAT character the kind of bit that never got as famous as Triumph the Insult Comic Dog, but still lives rent-free in the minds of people who stayed up too late watching NBC in the 2000s.

Cracked has a long tradition of highlighting behind-the-scenes stories from comedy from The Office to cult movies and late-night shows and the Raymond piece fits right into that tradition.
It treats this absurd hemorrhoid hero with the same respect you’d give a beloved movie character, which is part of the joke and part of the charm.

In the streaming era, when talk shows are clipped to death on social media, a character like Preparation H Raymond feels almost old-fashioned: a slow-burn bit that rewarded you for watching the whole show, ads and all.

What Preparation H Raymond Says About Comedy

If you strip away the cream and the ears (phrasing!), Preparation H Raymond is a perfect example of how late-night comedy works at its best:

• Start with something painfully mundane. Everyone has some embarrassing health thing they’d rather not discuss.
• Push it to the edge of absurdity. Turn that shame into a proud mission statement. Make it heroic. Make it weirdly wholesome.
• Commit 100%. The character only works if the performer plays it like the most natural thing in the world.
• Invite the audience in. Literally, in this case. Put the joke in their hands, in the form of a free tube.

It’s the difference between a cheap punchline and something you still remember decades later.
Plenty of shows make jokes about bodily functions; very few build a recurring folk hero around butt relief and make him beloved.

Extra: My Life as Preparation H Raymond – The Experience

Now, imagine living that life not as a viewer, but as the person under the ears.

You’re backstage at 30 Rockefeller Plaza.
The band is doing a sound check down the hall, cue cards are shuffled, stage managers are calling out time cues, and you’re in a small room trying not to ruin your makeup while laughing at how ridiculous your job is tonight: you are about to become the world’s most enthusiastic hemorrhoid evangelist.

The first time you put on the Raymond ears, you feel a tiny identity shift.
They’re not just props; they’re a signal that you’re no longer a writer hunched over a laptop.
You’re a character who honestly, deeply believes that what the world needs right now is soothing cream and eye contact.

A stagehand hands you a box heavy with Preparation H tubes.
You do a quick mental calculation: how many rows can you realistically hit in three minutes without tripping over somebody’s feet, the camera cables, or your own nerves?
The director reminds you: “Hit the center aisle first, swing left, circle back, and don’t block Conan’s angle when you head to the stairs.”

Then you hear it: “We’re back in five… four…” The theme music fades down, the applause swells, and Conan introduces you with that half-mocking, half-delighted tone that tells the audience, “Yes, this is very stupid, and yes, it’s exactly the kind of stupid you came here for.”

Stepping onto the stage as Preparation H Raymond feels strangely empowering.
You’re not embarrassed anymore; you’re on a mission.
The studio lights hit you, the band tags your theme, and you launch into your speech about generosity, comfort, and getting through “a long, difficult winter for the lower forty-eight inches.”

When you start walking through the aisles, something magical happens.
People don’t recoil from the awkwardness they lean into it.
Hands shoot out for tubes like you’re giving away smartphones instead of ointment.
Some audience members are laughing so hard they can barely get the words “thank you” out. Others clutch the tube like it’s a rare collectible.

Every reaction becomes part of the show.
Someone holds the tube up to the camera. Someone hides theirs under their jacket, which is even funnier.
You ad-lib a line to a guy in the front row who clearly brought his parents; the crowd loses it.
You’re not just delivering a bit you’re orchestrating a small, joyous social disaster.

Backstage after the segment, the adrenaline drop is real.
You peel off the ears, wipe off the makeup, and drop the remaining tubes back in the prop bin.
A fellow writer sticks their head in and says, “That was insane. We’re definitely bringing him back.”
You laugh, because of course you are.
As long as there are live audiences and people willing to giggle about their least glamorous problems, there’s room for Preparation H Raymond.

Over time, playing Raymond changes how you think about comedy and vulnerability.
You realize that the biggest laughs often come when everyone in the room silently agrees, “This is mortifying and that’s exactly why it’s funny.”
You see how much joy there is in naming the thing people are embarrassed to name, then wrapping it in warmth, silliness, and a theme song.

Years later, when clips resurface online and fans call Raymond an underrated classic, it feels oddly touching.
It means that somewhere out there, people still remember not just the joke, but the feeling of being in that room of laughing with strangers while clutching a tube of ointment you didn’t ask for, gifted by a man who looked like a royal family outcast with a heart of gold.

That’s the secret of life as Preparation H Raymond on Late Night with Conan O’Brien:
you’re not just selling a gag; you’re giving people permission to laugh at the parts of being human that aren’t glamorous, heroic, or Instagram-ready.
And once you’ve done that in front of a national audience, there’s very little left in life that can truly embarrass you.

Conclusion

“My Life as Preparation H Raymond on ‘Late Night with Conan O’Brien’” isn’t just a funny headline it’s a snapshot of a particular kind of late-night magic.
It’s the magic of taking something mundane and slightly horrifying, turning it into a recurring character, and discovering that audiences will cheer for anyone who shows up with commitment, kindness, and free relief in a tube.

In the end, Preparation H Raymond isn’t just a relic of early-2000s weird TV; he’s a reminder that the best comedy doesn’t always punch down or pretend to be cool.
Sometimes, it just walks down the aisle, looks you in the eye, and says, “You look like you’ve had a long week. Here this might help.”