Legendary comedian and late night host Conan O’Brien ended his smart and silly reign of nearly 30 years last June. To many, this inevitable moment came far too soon. Conan was at the top of his game, and though it had been nearly three decades, it felt like the late night party was just getting started. He continues to assure fans, however, that while his TBS show Conan might be over, he isn’t going anywhere. In addition to hosting his popular podcast Conan O’Brien Needs A Friend with his lovable assistant Sona Movsesian and producer Matt Gourley, he’s gearing up for his new show at his new home: HBO Max. The tall freckled fella told Deadline that he’s looking forward to creating more wacky content and being himself, saying, “What I’d like to focus on is the stuff that I think I’m particularly useful at or adept at. I want to double down on that… remotes and when I’m with real people in real situations, that’s exactly the kind of stuff I’m thinking about and want to do.”

But let’s go back to the beginning. Conan’s late night career started in 1993 on NBC, when he took over for David Letterman and hosted Late Night with Conan O’Brien until 2009. Most people had no idea who the young funnyman was because until then, he had never really been in front of the camera. He made a name for himself in the comedy business writing for Saturday Night Live and The Simpsons, two of the longest-running comedy programs of all-time, and then Lorne Michaels decided it was time everyone knew what the orange-haired genius was all about. And thank goodness he did!

Let’s look back at some of Conan O’Brien’s best remotes from Late Night with Conan O’Brien.

Conan Visits the Set of Martha Stewart Living

Conan-Martha Stewart

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No one knows how to disrupt a well-oiled kitchen operation quite like Conan. In this remote from 2002, lifestyle guru, food connoisseur, and businesswoman Martha Stewart gives Conan a tour of the homey set of her popular show Martha Stewart Living. Conan is in awe of the amount of counter space Martha has and struggles to tell the difference between a variety of salts. He also kicks a few kitchen hypothetical scenarios Martha’s way and the two enjoy some of the finest food in the land: spray cheese and beer. Also, what the heck kind of fruit is quince?

Conan Goes to the Deli

Conan Goes to the Deli

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An epic late night host needs an epic sandwich. Or, soup and a small house salad. Conan receives word that the long-standing New York City hotspot Stage Door Deli honored him with a sandwich, and naturally, decides to bring along a camera crew to check it out. He’s excited to join the company of other famous folks, such as Halle Berry, Eddie Murphy, Glenn Close, and Barbra Streisand, but is a little disappointed with his far-less exciting meal. How come Berry gets tongue and pastrami, and he only gets lettuce? Life just isn’t fair. And does anyone know who Jack Wagner is?

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Conan Goes Apple Picking with Mr. T

Conan Goes Apple Picking with Mr. T

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Nothing beats autumn on the east coast. The leaves are changing, the sun is shining, and apples are growing from trees! Conan and The A-Team star Mr. T grab their wheelbarrow and head to an apple orchard to pick some fruit. Mr. T brings his signature mohawk, chains, and rage to the idyllic family-friendly spot, and berates apples for not being good enough. Meanwhile, Conan scampers away and hides in a tree. Did the A-Team just get a new member? Probably not.

Conan Goes Wine Tasting in Napa Valley

Conan Goes Wine Tasting in Napa Valley

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What happens when you fill Conan with wine? In 2007, Conan did a week of shows in San Francisco and took advantage of the fact that he was close to Napa Valley, home of hundreds of the world’s most well-known vineyards. He swishes, spits, and swallows his way through the famous winery and reflects on Swiss methods of transportation. And, he discovers how surprisingly dirty some wine lingo sounds. “Okay, I just stuck the glass shaft into the bunghole, and you want me to put my finger over this?” Sit back, relax, and watch Conan enjoy the acoustics of the Spring Mountain Wine Cave.

Conan Helps Out During the NYC Transit Strike

Conan Helps Out During the NYC Transit Strike

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In December of 2005, New York City suffered a widespread public transportation strike. No subways, no trains, no taxis? No problem! Heartbroken to see so many of his fellow New Yorkers with no way of navigating the city, Conan rented a black van and offered his driving services to anyone that wanted them. But Conan does things a little differently than other drivers. He will root through your belongings, drink your hot chocolate, and stop to buy a Christmas tree. What would the Big Apple do without this tall jokester?

Conan Gets His Own G.I. Joe Doll

Conan Gets His Own G.I. Joe Doll

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Who do you think is more fit: G.I Joe or Conan O’Brien? The Late Night host heard that Hasbro was on the lookout for someone who embodies the physical characteristics of a G.I. Joe action figure and immediately threw his hat into the ring. In 1999, Conan popped by Hasbro’s headquarters in Cincinnati, Ohio to learn about the detailed process behind crafting the perfect doll. He suggests more realistic body types, tries to get the creators to fall in love with him, and uses a lot of white paint.

Conan Plays Old Timey Baseball

Conan Plays Old Timey Baseball

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Conan loves baseball and American history, so when he read in a newspaper that Old Bethpage Village Restoration in Long Island, New York has a team of dedicated people who play baseball the way it used to be played in the 1800s, well, he had to see for himself! Conan interviews some players and women in the stands (all of whom are dressed in historically accurate 1864 attire) and tries to get them to break character. He then dresses head-to-toe in an elaborate old timey uniform, loses his patience with his fellow teammates, and tries to convince the stubborn Nell, who’s waiting for her husband to return home from the Civil War, to go on a date with him. In an episode of Team Coco’s Inside Conan podcast, writer Kevin Dorff talks about the remote’s origins, and we hear years later from fan favorite Nell. Did her husband survive the war?

Conan Gives a Tour of the Late Night Offices

Conan Gives a Tour of the Late Night Offices

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In 2004, Conan’s Late Night had been on the air for over a decade and by then, had cemented itself as a late night fixture. You can understand his frustration, then, when NBC neglected to renovate the show’s offices. Employees are packed in like sardines and tripping over stacks of paper and piles of VHS tapes. Come on, what gives? In an attempt to convince the powers that be at 30 Rockefeller Center to fix the place, Conan spoke with his crew and took a tour of the run-down Late Night offices to expose its poor layout and its effects on the staff. And, he does a few “repairs” of his own while he’s at it. Have no fear! The offices were finally renovated in 2005.

Conan Becomes a UPS Deliveryman

Conan Becomes a UPS Deliveryman

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It’s been Conan’s life-long dream to be a UPS driver. And by “life-long” he means something he thought of doing on a whim. Conan suits up in brown and hops in the “package cars” for his ride-a longs before getting behind the wheel himself (and running over several cones in the process). Then he teams up with veteran driver Frank to hit the open road and do what they do best: deliver packages. Conan also has some trouble setting boundaries with the package recipients, and may or may not have trespassed.

Conan Goes to a Spa

Conan Goes to a Spa

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It’s stressful being a talk show host! That’s why Conan is way overdue for a relaxing day at the spa. He heads over to the Bliss Spa in New York to get a day of much-need pampering (which includes a facial, massage, and getting covered in carrots) and is sure to let the employees know of his many aches and pains. In addition to the occasional headache and fatigue, he can’t help but notice that his eyes randomly cross and that his bowls are both irregular and irresponsible. In typical Conan fashion, little is left to the imagination.

Conan Checks Out the Christmas Lights in Dyker Heights

Conan Checks Out the Christmas Lights in Dyker Heights

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Ho ho ho! It’s Christmas! New York around the holidays is always festive and full of cheer, but have you ever experienced Christmas in Brooklyn's Dyker Heights? This neighborhood is known for its over-the-top Christmas decorations and enthusiasm for the cozy holiday, attracting people from near and far to take in the sights. Conan had to see it for himself of course, and decided to visit some of the most decked-out homes on the block. Along the way, he gets to know the people behind the elaborate displays and realizes that his true calling in life might be to voice a giant animatronic Santa. Nothing says Christmas quite like John Travolta from Battlefield Earth.

Conan’s Dinner with Jordan Parts 1 & 2

Conan’s Dinner with Jordan

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Jordan, Jordan, Jordan. One of the most comforting aspects of Conan’s show is that he gives us a peek behind the curtain and introduces us to various members of his staff. The most infamous of the bunch is by far Jordan Schlansky, an uptight, mysterious associate producer on the show that Conan loves to humiliate. We really get to know him when he takes Conan out to his favorite Italian restaurant on the Upper East Side, where he educates him on the fine foods and explains how to have a proper eating experience. The best part? Conan couldn’t care less. Parts one and two of their dinner is just the beginning of this hostile bromance.

Stay tuned for Conan’s HBO Max show, which is expected to premiere later this year. New episodes of his podcast Conan O’Brien Needs A Friend air every Monday and Thursday wherever you get your podcasts.