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(Scene: A tropical beach backdrop with palm trees swaying, waves crashing, and Conan O’Brien standing dramatically in a Hawaiian shirt that’s at least two sizes too big. He holds a coconut drink—poorly balanced with a tiny umbrella—while wearing a lei around his neck.)
Conan O’Brien:
Aloha, ladies and gentlemen! That’s right, I’ve finally made it to Hawaii! And before you say anything—yes, I know I don’t exactly look like I belong here. I’m pale, lanky, and just one bad sunburn away from becoming a human lobster.
But this week, I’m throwing myself into the ultimate Hawaiian adventure, and I’ve brought a few equally ridiculous people along for the ride. We’re talking wild road trips, shark cage encounters, waterfall mishaps, and more seafood than my Irish digestive system is prepared for.
Now, I know what you’re thinking. "Conan, you’re not exactly the 'rugged island explorer' type." And to that, I say: You're absolutely right. That’s why I’ve enlisted some amazing, fun-loving, and possibly unhinged celebrities to help me navigate the chaos, including…
- Day 1 in Oahu: The Rock, Jack Black, and Bruno Mars! A trio that will out-surf, out-sing, and out-flex me within minutes.
- Day 2 in North Shore: Jason Momoa, Kevin Hart, and Auli’i Cravalho! If Kevin Hart doesn’t pass out from shark cage diving, it’ll be a miracle.
- Day 3 in Maui: Bill Murray, Emma Stone, and Kimié Miner! Because if you’re driving The Road to Hana, you need someone who knows no fear (or has no regard for speed limits).
- Day 4 in Big Island: Jeff Goldblum, Ryan Reynolds, and Makana! A mix of existential volcano wisdom, sarcasm, and some slack-key guitar magic.
- Day 5 in Kauai: Chris Pratt, Kristen Wiig, and the legendary Bette Midler! Because what’s a Hawaiian trip without a little Broadway diva energy?
And of course, each day, we have a local tour guide—Hawaiians who actually know what they’re doing and will try (and fail) to keep us from making complete fools of ourselves.
So get ready for epic landscapes, legendary food, dangerous stunts, and the occasional near-death experience—all narrated by me, a man who will most likely embarrass himself in at least four different ways per day.
Welcome to the Ultimate Conan Hawaiian Adventure! Let’s do this.
(Cue Hawaiian music, a wave crashes behind him, and Conan immediately gets knocked over.)
(Note: This is an imaginary conversation, a creative exploration of an idea, and not a real speech or event.)
Day 1 - Exploring Honolulu & Waikiki
Guests: Conan O’Brien, Dwayne "The Rock" Johnson, Jack Black, Bruno Mars
Tour Guide: Uncle Kimo
Scene: Sunrise at Diamond Head
(The group hikes up Diamond Head as the sun rises over Waikiki. Conan is already out of breath.)
Conan O’Brien: (huffing and puffing) Okay, pause. Whose idea was it to start our vacation with a hike? I thought Hawaiian vacations were supposed to be about relaxing.
Dwayne “The Rock” Johnson: (laughs) Conan, buddy, you wanted to see the best view in Oahu. No pain, no gain.
Jack Black: (gasping) Bro... I think I just unlocked a new lung condition. Can we get a sherpa? A tour bus? A gondola?!
Bruno Mars: (effortlessly jogging past them) Man, you guys are weak. I could run up this thing singing Uptown Funk.
Conan O’Brien: Great. I’m stuck on this death hike with Hercules, Kung Fu Panda, and Hawaii’s fittest pop star.
Uncle Kimo: (laughing) You guys are soft! Back in the day, Hawaiian warriors would run this crater barefoot to train for battle.
Jack Black: (dramatically falls to his knees) Well, I surrender. Somebody carry me.
Bruno Mars: Not it.
The Rock: (grinning) Alright, come on, Jack. Time to put those rock-hard calves to work.
(They finally reach the summit and take in the breathtaking view.)
Conan O’Brien: Okay... I admit... this is incredible. You win, Hawaii.
Jack Black: (panting) Agreed. Totally worth the impending leg cramp.
Scene: Breakfast at Koko Head Café
(The team enjoys Hawaiian-style brunch: loco moco, spam musubi, and macadamia nut pancakes.)
Conan O’Brien: So, tell me, what’s the most legendary Hawaiian breakfast dish?
Uncle Kimo: Oh, hands down, loco moco. It’s got rice, a juicy hamburger patty, a fried egg, and smothered in brown gravy.
Jack Black: (takes a bite) Holy mother of all breakfasts. This is a spiritual experience.
Bruno Mars: (nods) See? This is why Hawaiians are chill. You eat this and you don’t stress about anything.
The Rock: Yeah, but if you eat too much, you won’t fit into your Moana costume next Halloween.
Conan O’Brien: Okay, note to self: never order two loco mocos. (pushes plate away slightly)
Scene: Waikiki Beach – Surfing Challenge
(They take a surfing lesson. Conan, naturally, is struggling.)
Conan O’Brien: Alright, explain to me why humans willingly do this.
Bruno Mars: (laughing) Because it’s the best feeling in the world!
Jack Black: (wiping out instantly) Or... the most humiliating.
The Rock: (flawlessly catching a wave) You just gotta commit, man. Feel the wave. Become the wave.
Conan O’Brien: (getting crushed by a wave) I’M NOT BECOMING THE WAVE, THE WAVE IS BECOMING ME.
(Bruno Mars effortlessly rides a wave while singing “Just the Way You Are.” Jack Black dramatically belly flops into the water.)
Uncle Kimo: You know, ancient Hawaiian chiefs were the only ones allowed to ride the biggest waves. It was a symbol of power.
Jack Black: So... what you’re saying is, if I master this, I could be King of Hawaii?
Bruno Mars: (laughs) I think that title is already taken.
Conan O’Brien: Yeah, by The Rock.
The Rock: (grinning) Damn right.
Scene: Pearl Harbor & USS Arizona Memorial
(The tone shifts as they visit Pearl Harbor to pay respects.)
Uncle Kimo: (somberly) Over 1,100 sailors remain entombed here in the USS Arizona. It’s a place of deep respect and remembrance.
The Rock: This place reminds us of the sacrifices made for freedom.
Bruno Mars: My grandpa used to tell me stories about how Hawaii changed forever after this. It’s important to never forget.
Conan O’Brien: (nodding) This is one of those places where you just... stand still and take it in.
Jack Black: Yeah... It’s humbling.
(They take a quiet moment of reflection before moving on.)
Scene: Sunset at Tantalus Lookout
(After a long day, they relax with an incredible view of Honolulu.)
Jack Black: (deep sigh) Okay. I get it now.
Conan O’Brien: Get what?
Jack Black: Why people come here and never want to leave.
Bruno Mars: (smirking) Told you.
The Rock: (looking out over the city) There’s something magical about this place. No matter where I go, Hawaii is always home.
Uncle Kimo: That’s because Hawaii isn’t just a place. It’s a feeling.
Conan O’Brien: (mock serious) And that feeling... is leg pain from hiking Diamond Head.
Jack Black: (laughs) And a full stomach from loco moco.
Bruno Mars: And the rush of catching a wave.
The Rock: And the deep pride of Hawaiian culture.
Conan O’Brien: (smiling) Alright, I’ll admit it. Day 1 = success.
(They clink their drinks together as the sun sets over Waikiki.)
Day 2 - North Shore & Adventure in Oahu
Guests: Conan O’Brien, Jason Momoa, Kevin Hart, Auli’i Cravalho
Tour Guide: Aunty Leilani
Scene: Morning at Haleiwa Café – Breakfast Before Adventure
(The group gathers at a small, local café in Haleiwa for breakfast before their big day.)
Conan O’Brien: (reading menu) Okay, today I’m going to try something authentically Hawaiian.
Kevin Hart: Conan, last time you said that, you ended up crying over wasabi-laced poke.
Jason Momoa: (laughs) Yeah, Conan, you’re the least island-ready person I’ve ever met.
Auli’i Cravalho: How about some Haupia pancakes? Coconut custard on top. Super ono (delicious).
Kevin Hart: Or how about this... Spam and eggs. That’s real island food.
Conan O’Brien: (squinting) Spam? That’s what people eat when the grocery store is out of real food.
Aunty Leilani: Oh no, honey. Spam is Hawaiian gold. In World War II, fresh meat was scarce, so we got creative. Spam musubi is practically a national treasure.
Kevin Hart: (grinning) Yeah, Conan. It’s like Hawaii’s version of caviar.
Conan O’Brien: If that’s true, I’m officially uncultured.
(They all dig into breakfast, Kevin films Conan struggling with his first bite of Spam musubi.)
Scene: Shark Cage Diving – Kevin’s Worst Nightmare
(The group arrives at the North Shore, preparing for shark cage diving.)
Kevin Hart: NOPE. No. Absolutely not. I saw Jaws too many times.
Jason Momoa: Come on, man, this is the ultimate experience! These are Galapagos sharks, they’re harmless.
Kevin Hart: I don’t care if they’re vegan sharks, Jason! I’m not getting in that water.
Auli’i Cravalho: (grinning) Oh, come on. Moana would totally do this.
Conan O’Brien: Yeah, and if Moana does it, you have to, Kevin.
Kevin Hart: I swear to God, if a shark so much as looks at me funny, I’m punching somebody.
(They lower into the cage. Jason Momoa is relaxed. Auli’i is thrilled. Conan is dramatically clutching the bars. Kevin is screaming incoherently.)
Kevin Hart: THIS AIN’T RIGHT. THIS AIN’T RIGHT. THE SHARK JUST WINKED AT ME.
Jason Momoa: Dude, it’s literally just swimming.
Conan O’Brien: (pretending to be a nature narrator) And here we see Kevin Hart, a man in his natural state of pure terror.
(Auli’i calmly films Kevin while giggling. Jason fist-bumps a shark.)
Scene: Laniakea Beach – Turtle Spotting & Kevin’s Recovery
(The team watches Hawaiian green sea turtles basking on the shore.)
Conan O’Brien: See, Kevin? No sharks here. Just gentle, peaceful turtles.
Kevin Hart: Oh, I’m supposed to trust these things? Look at them! Plotting. Watching.
Auli’i Cravalho: (laughing) They’re literally sleeping.
Jason Momoa: Turtles are sacred in Hawaiian culture, man. They symbolize wisdom and longevity.
Aunty Leilani: In ancient times, Hawaiians believed honu (sea turtles) were guides for lost souls.
Kevin Hart: (muttering) Well, I was lost in that shark cage. Where was MY turtle guide?
(A turtle lazily blinks at Kevin. The group bursts out laughing.)
Scene: Lunch at Giovanni’s Shrimp Truck
(They stop for garlic shrimp, a famous North Shore meal.)
Conan O’Brien: (taking a bite) Oh. OH. This is heavenly.
Kevin Hart: This is the only reason I forgive you all for today.
Jason Momoa: (grinning) You know, if you mix the shrimp sauce with some poi—
Conan O’Brien: NOPE. I draw the line at purple paste.
Auli’i Cravalho: Poi is amazing! It’s a staple food here, made from taro root.
Kevin Hart: You lost me at root. If I wanted to eat dirt, I’d just go outside.
Scene: Waimea Valley – Waterfall Swimming
(They arrive at Waimea Valley, a lush botanical paradise, leading to a beautiful waterfall pool.)
Auli’i Cravalho: (excited) Okay, waterfall swimming is a must.
Conan O’Brien: Oh sure, what could possibly go wrong?
Kevin Hart: I already told y’all, water is not my friend today.
Jason Momoa: Oh, we’re doing this.
(Jason jumps first, doing a perfect cannonball. Auli’i dives in gracefully. Kevin and Conan stand at the edge, debating.)
Conan O’Brien: Kevin, as your trusted travel guide, I say you should go first.
Kevin Hart: Oh yeah? Well as my therapist, I say I ain’t doing it.
(Jason climbs back up, picks up Kevin like a small child, and jumps in with him. Kevin’s screams echo through the valley.)
Scene: Sunset Beach – Big Wave Surf Watching
(They dry off at Sunset Beach, watching surfers ride massive waves.)
Conan O’Brien: Look at these maniacs. Who sees a 20-foot wall of water and says, "Yep, let’s ride that?"
Jason Momoa: That’s what makes them legends, man.
Auli’i Cravalho: You know, Hawaiians have been surfing for over a thousand years.
Aunty Leilani: Back in the day, only the ali’i (Hawaiian royalty) were allowed to ride the biggest waves.
Kevin Hart: (dead serious) That rule should still exist. Because regular people have NO BUSINESS doing this.
Scene: Dinner at Haleiwa Joe’s & Closing Thoughts
(They wrap up the day with dinner, reminiscing about the madness.)
Conan O’Brien: Alright, day two recap. Who had the best moment?
Jason Momoa: Me, obviously. I bonded with a shark.
Auli’i Cravalho: I’d say Kevin’s waterfall scream.
Kevin Hart: DISRESPECT. I SURVIVED.
Conan O’Brien: And what did we learn?
Kevin Hart: That I should’ve stayed in the hotel.
Jason Momoa: That Conan will never fully embrace island life.
Auli’i Cravalho: That Spam musubi is an elite breakfast.
Aunty Leilani: And that Hawaii is about adventure, storytelling, and facing your fears.
Kevin Hart: Well, my fear got FACED. And it looked like a shark.
(They toast to another wild day as the sun sets over the North Shore.)
Day 3 – Maui & The Road to Hana
Tour Guide: Cousin Koa
Scene: Sunrise at Haleakalā Crater
(The group arrives at the summit of Haleakalā, the dormant volcano, to witness the legendary sunrise. It’s breathtaking… but also freezing cold.)
Conan O’Brien: (shivering) WHY did no one tell me Hawaii could be this cold?! I thought we signed up for paradise, not Antarctica.
Emma Stone: (bundled in three jackets) I was lied to.
Bill Murray: (completely unfazed, sipping coffee in shorts and a Hawaiian shirt) You guys need to embrace the chill. This is spiritual weather.
Kimié Miner: (smiling) My grandma used to say that the sunrise here is a gift from the gods. It’s a reminder that every day is a new beginning.
Cousin Koa: (nodding) Ancient Hawaiians believed this was the home of Maui the demigod. He lassoed the sun right over there to make the days longer.
Conan O’Brien: So you’re telling me, a ripped dude with a magical rope kept me from sleeping in today?
Emma Stone: Honestly, respect.
(The sun rises, casting an unreal glow over the crater. It’s silent, peaceful… until Bill Murray starts humming “Also sprach Zarathustra” from 2001: A Space Odyssey.)
Scene: Breakfast at Kula Lodge
(The team heads down to the lush slopes of Haleakalā for a well-earned meal.)
Conan O’Brien: (digging into pineapple pancakes) THIS is what I needed. Warmth. Food. No altitude sickness.
Bill Murray: You’re acting like you just climbed Everest.
Emma Stone: To be fair, he whined the whole way up.
Kimié Miner: Did you guys try the lilikoi butter on your toast? Game-changer.
Conan O’Brien: Okay, I admit, Hawaii keeps winning.
Scene: The Road to Hana Begins – Bill Murray Takes the Wheel
(They rent a Jeep and hit the Road to Hana, a winding, 64-mile drive with over 600 curves.)
Conan O’Brien: Okay, who’s driving?
Bill Murray: (grabbing the keys) I got this.
Emma Stone: (nervous) I feel like Bill Murray should never be the driver.
Bill Murray: Trust me, I’ve driven weirder things.
(Bill floors it. The Jeep swerves through the first set of tight jungle roads.)
Conan O’Brien: OH GOD. WHO GAVE HIM PERMISSION?!
Kimié Miner: This road is supposed to be peaceful.
Emma Stone: Bill, slow down! There are like 700 cliffs here!
Bill Murray: (calmly) If it’s my time, it’s my time.
(They white-knuckle it through the first few miles, screaming at every turn.)
Scene: First Stop – Twin Falls
(They pull over for a short jungle hike to Twin Falls, a stunning waterfall with a natural pool.)
Cousin Koa: (leading the way) This is one of the first hidden gems on the Road to Hana. Fresh waterfall, perfect for swimming.
Emma Stone: (hesitant) Should I be concerned about… wild things in the water?
Kimié Miner: Just watch for eels.
Conan O’Brien: I KNEW IT. EVERYBODY OUT.
Bill Murray: Eels are just snakes who love the water.
Emma Stone: THAT DOESN’T MAKE IT BETTER.
(Kimié starts singing a soft Hawaiian song by the waterfall. The peaceful moment is ruined when Bill cannonballs into the pool.)
Scene: Lunch at Hana Farms Roadside Stand
(They stop for fresh banana bread and tropical fruit.)
Conan O’Brien: Okay, this banana bread is actually illegal-level good.
Emma Stone: I feel like we need to smuggle this off the island.
Bill Murray: (handing out passionfruit) Try this. It’s Hawaiian candy, straight from nature.
Kimié Miner: We grow some of the best fruit in the world here.
Cousin Koa: Did you know, back in the old days, Hawaiians used fruit to heal wounds?
Conan O’Brien: I believe it. This mango just healed my soul.
Scene: Wailua Falls & The Seven Sacred Pools (Oheo Gulch)
(They hike through bamboo forests to one of Maui’s most magical spots—cascading waterfalls and pools.)
Emma Stone: This place looks like a literal movie set.
Bill Murray: It is.
Cousin Koa: Actually, this area was sacred to Hawaiian royalty. The ali’i (chiefs) would bathe here to cleanse themselves before important ceremonies.
Conan O’Brien: And now, I, an Irish guy from Boston, will attempt to do the same.
(He steps into the pool, immediately slips and falls flat on his back.)
Emma Stone: (dying of laughter) Okay, highlight of the trip.
Scene: The Drive Back – Bill’s Surprise Detour
(On the way back, Bill randomly turns onto a dirt road.)
Emma Stone: Bill, what are you doing?
Bill Murray: Vibes, Emma. I’m following the vibes.
Cousin Koa: Oh man, you actually turned onto a real secret spot.
Kimié Miner: Wait… is this Red Sand Beach?!
Conan O’Brien: (eyes widening) We just accidentally discovered buried treasure.
(They step out onto a hidden, rust-colored beach, completely empty except for a few sea turtles.)
Scene: Sunset Dinner at Mama’s Fish House
(They arrive at one of the most famous restaurants in Hawaii for an epic meal.)
Conan O’Brien: (cutting into fresh mahi-mahi) This meal is the final boss of seafood.
Bill Murray: I feel like I just ascended.
Emma Stone: I officially want to live here forever.
Kimié Miner: That’s the magic of Maui.
Conan O’Brien: Alright, Day 3 recap.
✔ Best Moment: Secret Red Sand Beach discovery
✔ Worst Moment: Conan slipping into sacred waters
✔ Funniest Moment: Bill’s questionable driving
✔ Best Quote:
"Eels are just snakes who love the water."
Day 4 – Big Island Adventures
Guests: Conan O’Brien, Jeff Goldblum, Ryan Reynolds, Makana (Local Slack-Key Guitarist)
Tour Guide: Tūtū Kalea
Scene: Early Morning Flight to Hilo
(The team boards a tiny inter-island plane. Conan looks uneasy.)
Conan O’Brien: (clutching armrests) I have several questions about this aircraft. Mainly: is it held together with duct tape?
Ryan Reynolds: Don’t worry, Conan. I asked the pilot if he passed flight school and he just gave me a thumbs-up.
Jeff Goldblum: Ah, yes, yes. The thrill of travel! The fragility of human existence… (pauses for dramatic effect) …delightful.
Makana: You guys are soft. Back in the day, my ancestors navigated the Pacific using only the stars.
Conan O’Brien: And here I am, praying for Wi-Fi.
*(The plane lands. Conan kisses the ground.)
Scene: Breakfast at Ken’s House of Pancakes
(They stop at the famous diner for a giant Hawaiian-style breakfast.)
Conan O’Brien: (reading menu) Okay, I need to try something uniquely Hawaiian.
Jeff Goldblum: Ah, yes! The local flavors! The symphony of gastronomic ecstasy!
Makana: Get the loco moco. Rice, hamburger patty, fried egg, drenched in brown gravy.
Ryan Reynolds: So… basically a cheat meal that lasts three days.
Conan O’Brien: (takes a bite, eyes widen) I think I just saw God.
Jeff Goldblum: Yes, yes… the umami… the harmony of textures… an existential event.
Scene: Hawaii Volcanoes National Park – Lava Time
(They arrive at the park, staring at the massive, steaming caldera.)
Conan O’Brien: Yep. That is a giant hole of fire. Why are we going closer?
Ryan Reynolds: For science! Or stupidity! Either works.
Tūtū Kalea: (wise and calm) Pele, the Hawaiian goddess of fire, lives here. It is said she tests those who visit her land.
Jeff Goldblum: Ah! A test! A cosmic audition for survival. I love it.
Conan O’Brien: If Pele tests me, I will fail immediately.
(They hike to see fresh lava flows.)
Ryan Reynolds: Whoa. This looks like Mordor.
Conan O’Brien: If we see one ring, we’re out.
Tūtū Kalea: (grinning) You know, if you take lava rocks home, bad luck follows.
Ryan Reynolds: Good to know. Conan, take one.
Conan O’Brien: WHY WOULD YOU WISH THIS UPON ME?!
Scene: Punalu’u Black Sand Beach
(They arrive at the legendary black sand beach, where sea turtles rest on the shore.)
Jeff Goldblum: The contrast, the texture, the juxtaposition of nature’s palette! Spectacular.
Conan O’Brien: Can we talk about how weirdly HOT this sand is?!
Ryan Reynolds: It’s black. It absorbs heat. Were you homeschooled?
Makana: Hawaiians believe sea turtles (honu) bring wisdom and guidance.
(One turtle slowly turns toward Conan.)
Ryan Reynolds: Dude. He’s judging you.
Conan O’Brien: He sees my past sins.
Scene: Akaka Falls – Jungle Adventure
(They hike to the stunning 400-foot waterfall.)
Jeff Goldblum: A liquid symphony! A cascading testament to the chaotic beauty of physics!
Conan O’Brien: I have never heard anyone describe a waterfall like that.
Ryan Reynolds: I have, but only in Goldblum movies.
Tūtū Kalea: Long ago, warriors would bathe here before battle. It was a ritual of strength.
Conan O’Brien: Yeah, well, I’m no warrior. I’m mostly limbs and regrets.
(Ryan shoves Conan toward the waterfall. Conan flails, but catches himself.)
Conan O’Brien: You’re trying to kill me. I KNEW IT.
Scene: Dinner at Pineapples in Hilo
(The team winds down with fresh seafood and tropical drinks.)
Makana: (playing slack-key guitar) This is the sound of old Hawaii.
Jeff Goldblum: Hypnotic! Enchanting! I feel transcendent.
Ryan Reynolds: I feel like a cocktail should be named after you.
Conan O’Brien: Alright, Day 4 recap.
✔ Best Moment: Lava hikes & Ryan trying to curse Conan
✔ Worst Moment: Conan getting judged by a turtle
✔ Funniest Moment: Goldblum’s volcanic poetry
✔ Best Quote:
"If we see one ring, we’re out."
Day 5 – Kauai & The Na Pali Coast Adventure
Guests: Conan O’Brien, Chris Pratt, Kristen Wiig, Bette Midler (Local Celebrity)
Tour Guide: Captain Makoa
Scene: Early Morning Flight to Kauai
(The group boards another tiny inter-island plane. Conan looks even more nervous than Day 4.)
Conan O’Brien: Okay. New rule. No more tiny planes. This is basically a glorified kite.
Kristen Wiig: (calmly drinking coffee) Conan, it’s 30 minutes. Just relax and pretend you’re in a movie montage.
Chris Pratt: (laughing) What’s the worst that could happen?
Conan O’Brien: WHY WOULD YOU SAY THAT?!
Bette Midler: Don’t worry, sweetheart. If this plane goes down, I will personally float you to safety.
*(Plane lands. Conan looks deeply betrayed but alive.)
Scene: Waimea Canyon – "The Grand Canyon of the Pacific"
(They arrive at the massive red-rock canyon with breathtaking views.)
Chris Pratt: WHOA. This is like Jurassic Park in real life.
Captain Makoa: Well, actually... Jurassic Park was filmed here.
Conan O’Brien: Oh great. So now I have to worry about sharks AND velociraptors?
Kristen Wiig: I mean… if anyone here gets eaten first, it’s you.
Bette Midler: (mock serious) I’ve been saying that for years.
(Chris pretends to be a velociraptor, sneaking up behind Conan. Kristen films as Conan screams.)
Scene: The Secret "Forbidden" Jungle Trail
(Captain Makoa leads them on a "not exactly legal" jungle hike.)
Captain Makoa: This is a locals-only trail to a hidden waterfall.
Bette Midler: (grinning) I like this guy.
Conan O’Brien: (tripping over a root) Yeah, well, this trail doesn’t like me.
Chris Pratt: You need a machete.
Kristen Wiig: You need better life choices.
(They reach a gorgeous, secret waterfall.)
Bette Midler: This is where I want to be forever.
(Kristen and Chris cannonball into the water. Conan hesitates.)
Chris Pratt: What’s wrong?
Conan O’Brien: I’m just considering all the ways this could go wrong.
Bette Midler: Honey, if I can do it, so can you.
*(Bette pushes Conan in. The splash is ridiculous.)
Scene: Na Pali Coast Boat Tour – Dolphins & Chaos
(They board a speedboat for one of the most stunning coastlines in the world.)
Captain Makoa: Na Pali means “The Cliffs.” Only accessible by boat or helicopter.
Chris Pratt: This is literally the most beautiful place I’ve ever seen.
Kristen Wiig: (mock serious) And now… we live here.
(A pod of dolphins swims alongside the boat.)
Conan O’Brien: (gasping) OH MY GOD. THEY LIKE ME.
Bette Midler: Don’t flatter yourself. They like everyone.
*(Captain Makoa suddenly cranks the speed, sending Conan flying backward.)
Conan O’Brien: (yelling over the wind) I DIDN’T SIGN UP FOR THIS!
Chris Pratt: (laughing) THIS IS AMAZING.
Scene: Sunset at Poipu Beach – Final Dinner Together
(They arrive at a beachside restaurant for their final dinner.)
Kristen Wiig: (sighing) This week was ridiculous.
Chris Pratt: Best trip ever.
Conan O’Brien: Worst and best trip ever.
Bette Midler: That’s Hawaii, sweetheart.
Captain Makoa: So, what was your favorite moment?
✔ Kristen Wiig: Conan screaming about sharks.
✔ Chris Pratt: Secret waterfall jump.
✔ Bette Midler:
Pushing Conan into the water.
✔ Conan O’Brien: (deadpan) Surviving.
(They toast as the sun sets over the ocean, ending the most insane Hawaii trip ever.)
Final Reflection by Conan O’Brien – Closing Thoughts on the Ultimate Hawaii Adventure
(Scene: A quiet beach at sunset. Conan stands barefoot in the sand, the ocean waves gently rolling in. His Hawaiian shirt is now fully unbuttoned, his hair is messier than usual, and his skin has a definite sunburn despite wearing SPF 100.)
Conan O’Brien:
Well, folks… we did it. Five days. Five islands. And somehow, against all odds, I’m still alive.
Let’s take a moment to reflect on what we’ve learned:
✔ Hiking Diamond Head at sunrise is breathtaking—but also a cruel prank on pale people.
✔ Sharks don’t actually want to eat Kevin Hart—but that didn’t stop him from screaming like they did.
✔ Bill Murray should NEVER be allowed to drive on the Road to Hana.
✔ Volcanoes are hot, Black Sand Beach is hotter, and Ryan Reynolds will absolutely try to curse you with bad luck.
✔ Chris Pratt is still convinced dinosaurs are real, and Bette Midler WILL push you into the ocean.
But beyond the chaos, the wipeouts, and the questionable life choices, this trip reminded me of something deeper.
Hawaii isn’t just about the breathtaking views, the incredible food, or the warm waters. It’s about the people. The culture. The spirit of Aloha.
Everywhere we went, we met locals who welcomed us like family—from the tour guides who somehow didn’t abandon us mid-trip, to the musicians who filled our nights with the sounds of old Hawaii, to the strangers who laughed as I wiped out spectacularly on a surfboard.
There’s something magical about this place. Something that makes you slow down, breathe, and appreciate how beautiful life can be.
So as we wrap up this journey, I just want to say:
To Hawaii—thank you. Thank you for the adventure, the laughter, and for only mildly humiliating me.
And to all of you watching, if you ever get the chance, come here. See it. Feel it. Eat an unreasonable amount of loco moco.
As for me? Well… I think it’s time to finally lie down and take a very long nap.
*(A wave crashes behind him, knocking him off his feet one last time. The screen fades to black as the credits roll, set to Bruno Mars playing a Hawaiian version of "Just the Way You Are.")
Short Bios:
- Conan O’Brien – Legendary late-night talk show host, comedian, and world traveler known for his self-deprecating humor, quick wit, and adventurous spirit.
- Dwayne “The Rock” Johnson – Actor, former WWE champion, and Hawaiian-born superstar known for his charisma, fitness, and deep love for his Polynesian heritage.
- Jack Black – Comedic actor, musician, and all-around entertainer, famous for his energetic personality and love of spontaneous musical performances.
- Bruno Mars – Grammy-winning singer-songwriter from Hawaii, known for his smooth vocals, electrifying performances, and deep connection to island culture.
- Jason Momoa – Hollywood action star and Hawaiian native, best known for Aquaman and his love of surfing, adventure, and Polynesian traditions.
- Kevin Hart – Stand-up comedian, actor, and entertainer known for his high-energy humor, rapid-fire storytelling, and hilarious over-the-top reactions to extreme situations.
- Auli’i Cravalho – Hawaiian actress and singer, the voice of Moana, celebrated for her authentic representation of Polynesian culture and infectious optimism.
- Bill Murray – Iconic comedian and actor, famous for his unpredictable antics, dry humor, and philosophical outlook on life.
- Emma Stone – Oscar-winning actress with sharp comedic timing and a natural ability to keep up with Conan’s quick-witted humor.
- Kimié Miner – Hawaiian singer-songwriter known for her soothing island-inspired music and deep roots in Hawaiian culture.
- Jeff Goldblum – Actor, jazz musician, and master of quirky, existential musings, bringing his unique energy to every adventure.
- Ryan Reynolds – Actor, entrepreneur, and comedic genius known for his sarcastic wit, quick comebacks, and love of pranking his friends.
- Makana – Hawaiian slack-key guitarist and singer, preserving traditional Hawaiian music while adding a modern twist.
- Chris Pratt – Actor known for his roles in Guardians of the Galaxy and Jurassic World, bringing charm, humor, and a love of adventure.
- Kristen Wiig – Comedic actress and writer, famous for her improv skills, hilarious unpredictability, and deadpan humor.
- Bette Midler – Legendary entertainer, singer, and actress from Hawaii, known for her Broadway flair, quick wit, and larger-than-life personality.
- Uncle Kimo – Local Hawaiian tour guide, wise storyteller, and the ultimate source of hidden island secrets and fun facts.
- Aunty Leilani – North Shore expert and cultural guide, sharing Hawaiian traditions, history, and the best food spots on the island.
- Cousin Koa – Laid-back, thrill-seeking Maui tour guide who knows every off-the-beaten-path spot and how to make any drive an adventure.
- Tūtū Kalea – Wise Hawaiian elder and spiritual storyteller, sharing ancient legends, volcanic myths, and a deep connection to the land.
- Captain Makoa – Fearless Kauai boat captain with unmatched knowledge of the Na Pali Coast, plus a few thrilling, “totally safe” surprises.
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