Stephen Colbert Challenges You to an Ocean Race

He’s done exactly one distance race. He finished dead last. But that hasn’t stopped the host of “The Colbert Report” from issuing an open challenge to anyone interested in lining up against him at the start of the OnDeck Charleston to Bermuda Race. An extended version of the interview that appeared in our May 2011 issue.

May 12, 2011
Sailing World


“I may not know much about sailing, but I know I can beat you to Bermuda.” Courtesy Comedy Central

**Stephen Colbert’s first offshore racing experience, the 2005 Charleston to Bermuda Race, couldn’t have gone any worse. **The 45-foot cat ketch on which he sailed finished dead last. In fact, it took his crew so long to reach Bermuda, they arrived two days after the awards ceremony. But as unequivocally bad as it was from a racing perspective, as an experience, it was equally as profound. In fact, the normally glib 46-year-old, who hosts the satirical news show “The Colbert Report” on Comedy Central, says he has trouble finding the words to accurately explain why he enjoyed the 777-mile race so much, and why, come May 21, he’ll do it again.

What’s your sailing background?

I grew up right on Charleston Harbor, right across from the Carolina YC. The regattas were right outside my window. I wasn’t allowed to go sailing because I don’t have an eardrum in one ear and I couldn’t get water in my ear. It just drove me crazy. My mom felt so badly for me, that when I was 20, my doctor said, it’s healed enough—the thing that was wrong was still wrong, but it was better—he said, “You can go out there now.” My mom said, “OK, I’ll get you sailing lessons.” I said, “I don’t really want to now.” Which, of course, really upset her, because to her I was still a little boy. But, I said, to hell with it. I’d moved on.


So I kind of just left it behind. I’d done a little sailing, I’d snuck behind her back, and capsized, and got in trouble. But I hadn’t really done that much sailing, but the little I’d done I had enjoyed.

Then [in 2005] when I was 41, a friend called up and said, “The C2B [Charleston to Bermuda] is this year. I know somebody who’s got a boat, and you know almost all the guys on it. Do you want one of the berths on the boat? I asked my wife, and she said, “Yes. Go.” She shocked me. That was my introduction to serious sailing. I just loved it.

This past summer when we were down in Charleston—I hadn’t decided to do the C2B this year, the Charleston to Bermuda that OnDeck is doing. One day I was looking out, it was a beautiful day; I was down there for a couple of weeks. I actually called up OnDeck, not knowing I was calling up OnDeck, because they took over the maritime center in Charleston, and rented a Beneteau to take it out. Then I found out they were running the race and that’s how the whole thing started with me back involved with them again.


Tell us about that 2005 race?

As a race, it was a complete disaster. But as just sort of an experience at sea it was fantastic. It was hard, a lot of it, because maybe our equipment wasn’t as ready as we should’ve had it. We lost both of our heads, we ran out of diesel so we couldn’t charge our batteries. We ran out of water more than a day before arriving. We had some bottled water left, which I had to hide around the boat—I was the rationing officer. Our sat phone died, our halyards fouled so we couldn’t raise sail at one point. We were becalmed for two days. It was a crashing disaster in every direction. Yet, at the same time, what struck me was that for all the hardship of it, for everything that went wrong, the entire experience was sublime. Even the becalmed madness of the two days in the middle of it was just beautiful. That’s something that’s very hard to explain if you’ve never been out there. Admittedly that’s my only experience in mid-ocean sailing—I’ve done more sailing since then—but that mid-ocean sailing, it’s just hard to explain what is so profound about it. That’s why I want to go do it again, to reconnect with that feeling.

Did you break the head?


No, I don’t think it had been pumped out since the Carter administration. It was so full that you couldn’t even open the ocean cocks to drain it. Nothing would move. And that was Day 2 and it was a seven-day sail. So that led to some, what I like to call, crusty seamanship. It was 19th-Century yachting. It was a bucket brigade. We had a code we would yell. We had a bucket, and as we were coming up we would yell either “Code Yellow” or “Code Brown” and the decks would just clear either way. It’s not a very complex code, but we were trying to convey something very clearly to the people on deck.

How are you going to ensure that this race goes better?

This time it’s going to be on a Farr 65, and someone else is responsible for making sure it’s all provisioned and tuned, and that the heads have been pumped out. So hopefully since there’ll be professionals responsible for that, it’ll be in better shape. And it’ll be bigger so we won’t be hot-bunking, which we had to do the first time because there were only four berths and there were eight guys, so we were always switching out. The bed never got cold. For the first few days we were up together all the time, then we would catch a little sleep here and there. I think the longest we slept at any one time was four hours, for those seven days, because of the watch system we were on. I think we have more guys this time so we’re on three watches so we’ll have six hour sleeps instead of three or four hour sleeps. So bigger boat, more watches, hopefully the water doesn’t run out. That’ll be nice.


Is it your effort? Are you selecting the crew?

It’s all the same guys that went last time and then there will be a couple of other guys who come along, but we’re not entirely sure who else. But I want all the same guys. And I want to win this time.

You can’t do any worse.

Exactly. It’s not necessarily my effort; it’s all of our effort. But I want a lot of people to race. This is my life, not my character, but I’m happy to talk about it on my show and talk about it in the press. The more boats that do this, the more fun it’s going to be. I’m just very excited about getting a bunch of people out on the ocean, having people back home following them on the GPS on the website. I’m not really an athlete, so this is the closest I come to being sporting.

**Do you have a title on the boat? **

I’ve been made admiral of the fleet. I’m captain of the boat, but I’m admiral of the fleet. I’ll try not to get drunk with power.

What will be your prime contribution to the effort?

Panache. Je ne sais quoi. Hopefully, a sponsor who can pay for everything. [Ed’s note: Colbert has since signed Audi to sponsor his entry in the race]. Last time I was chaplain, cook, and morale officer. I was also the guy who pumped out the head by hand.

**That race has endured a couple of very light-air weather patterns. Which means you, and the rest of the fleet, are likely to get the snot knocked out of you this time around, law of averages and everything. **

It’s not that likely that time of year. But you’re right, given how unprepared we were last time we were really lucky it was so light. We had some gusts to 25 knots and that was about it.

If you do see some gale-force winds, will you be going up on deck to put in the third reef, or will you employ the “I’m too famous and too important to risk going out in that weather” excuse?

I’ll absolutely do it. [In 2005] our radar reflector got fouled in our main halyard. The lower lashing broke, but the top didn’t, so it swung around the mast like a tetherball. Our sails had been down because the race had been called, because it had been becalmed for two days, and we were motoring. We ran out of diesel before we made port, so we had to raise the main sail, but couldn’t. And we had to send somebody up in the bosun’s chair to cut it free. I volunteered. I said, “No, I’m not too big for my britches.”

Did you get selected?

No, the captain said, “It’s my responsibility, I’ll go up.” We were pitching around pretty badly. We had rocky seas, no motor, and sun was going down. And the mast track was really sharp. We were really worried that he was going to get cut to ribbons swinging by that thing. At the last minute—we had him in the chair, ready to pull him up—the radar reflector busted off on its own accord. It was an unbelievably serendipitous event. It busted off, hit the boom, banged off over our heads, and fell into the water.

We started screaming, laughing, and jumping up and down because we didn’t have to send him up. At that moment there was this burst of air next to the boat and we were all looked over and saw this whale roll slowly once and go back down under the water. Some of the others said they saw it show its flukes off the stern and disappear for good. But I kept looking right where it had been when it first came up. I swore to God that whale was telling us: “Stop celebrating. Your boat is completely f$%&ed up and you’re still 100 miles away from Bermuda. Why are you so happy?” It was really an inexplicable emotion and an unbelievable surprise. You can’t reproduce those moments. I’m looking forward to all the surprises the ocean has.

It was a message from Poseidon, “I’m watching you guys, don’t push me.”

Exactly. “We have given you such a free ride so far. Don’t f#%& this up.”

**On any distance race, the personal gear is limited… **

I learned that.

You didn’t roll your wheelie bag onto the boat?

I did not. I brought a duffel. But I did bring a blue blazer because it ends at the Royal Bermuda YC.

Right, you’ve got to have one in case you win.

In case? What are you talking about?


So this time around, what non-essentials are you going to try to sneak onboard for the trip?**

It was a dry cruise last time. The captain said, “I want to be clear, this is not a booze cruise. This can be dangerous business and I want everybody sharp. No one’s to bring any alcohol.” After that whale came up and drifted away from the boat, the captain said, “OK, wherever you’re hiding it, you can bring it out.” And every single person had brought liquor on the boat. Then we all had a cocktail. So I suppose I’ll bring a bottle of gold rum. You know what I’ll bring, an XM radio. It’s not supposed to work that far out, but it does, it works all the way to Bermuda. That’s what I learned last time.

So you can keep up on things?

I can listen to a little CNN, what’s going on in the news back home. But I can’t do anything about it. That’s the greatest thing: with my job, I have to keep my head so to ground on what’s happening every minute, that I love being someplace where I can’t respond.

Don’t we all?

How many places are there left where you get to do that in the world. 500 miles out, you really are in the middle of nowhere.

What’s the latest with your challenge to Sir Richard Branson?

He said no. Virgin America is launching Chicago that week. They’ve worked for years to get the placements, and he’s there for the launch of every major city. The launch date is in the middle of the race. I’m going to have him on the show and mock him about it, and see if I can get him to change his mind. In the meantime, he says I can borrow the term, Greatest Sailor in the World.

Isn’t that a title he gave to himself?

I’m going to accept it. I don’t care if it’s a false term. I’ll take it. I don’t believe there is a place of Narnia, but I’ll take Aslan’s title if he’s willing to give it to me.

What sort of coverage of the race, before during or after, are you planning for your show?

There’s a cult that says the world is going to end on May 21, 2011. That’s why the race starts on May 21, because I’m leaving the country before the rapture. If I get raptured, it’s better to be at sea because I’m not going to bump my head on anything as I get raptured up. And if I’m not raptured, if I’m left for the tribulation, I want to be in international waters, so God can’t extradite me, because I don’t think he has an extradition treaty with Neptune. That’s one of the ways I will talk about it on the show.

I also will encourage other people to challenge me because I have declared myself to be the Greatest Sailor in the World. Since Sir Richard Branson forfeited, I’m the Greatest Sailor in the World. One thing that’s sincerely made me happy is with the economy the way it is, the last two sailings of the C2B have been very sparse, but I think they already have more boats committed at this point than they had even the year I did it. It’s my hometown, I’d like this race to be bigger.

I challenge anyone if they think they can beat me. I’ll see you on the dock and I’ll see you in Bermuda and I’ll throw the party if you win.

So it sounds like sailing is getting the patented “Colbert Bump”?

I am bumping sailing. I am America and so this is the real America’s Cup.

Courtesy Comedy Central
**”If I can’t beat you over the line, then I’ll sink you!” **

So does that mean Larry Ellison and Oracle Racing are competing for the false America’s Cup?

Ellison’s a fraud, and if he wants to prove me otherwise, he can meet me in Charleston and race me.

Pop Quiz Time: What are the ingredients in a Dark N Stormy?

Ginger beer, and dark rum, and lime.

OK, what specific brand of rum?

Bacardi Dark?

Close, Goslings.

Goslings is one of the sponsors of the race, damn! I got dark rum right, c’mon.

Half credit. Question No. 2. Have you ever experienced the Gold Bond handshake? This is when someone comes up from below, after dusting their privates, shakes your hand, leaving a behind a nice white residue, and you look at your hand and think…

I know the last place that [other person’s hand] was. No, but I have to remember to get some Gold Bond. One thing I did learn was how easy it is to get swamp ass. I had an historic case of swamp ass. You know what’s tough swimming in the middle of the ocean?

Tough as in scary?

When we were becalmed out there for two days, the first day we said, “Hey, let’s go for a swim.” Some people stayed on the boat, so it wouldn’t drift away from us. We put out some lines and some bumpers and we all dove in. Until you look down with goggles on. It was so clear, as clear as air, and I felt immediately like I was falling through the infinitely receding sunbeams below you. And also that something big was about to come up from the depths.

I know exactly what you mean. It almost gives you vertigo.

We were in 15,000 feet of water. It’s absolutely freaky. The odd thing is, it doesn’t get dark, it just gets away from you. It’s like looking at the sky, but down. I’m just afraid it’s going to be filled with a tooth-filled mouth. Every single person who looked down immediately said: “Put out the ladder, I’m coming up.” And we didn’t go swimming again. Plus the next day we woke up, and as far as the eye could see, it was Portuguese man-o-war.

Do you have any sailing heroes?

Christopher Columbus. Magellan. No, I don’t have any sailing heroes. I wish I did.

What about a favorite sailing song?

Farewell and Adieu You Fair Spanish Ladies, I supposed. Farewell and adieu you ladies of Spain for we’ve received orders to sail back to Boston and won’t be seeing you again.

Going the more classical route?

I‘m going the Orca from Jaws, Captain Quint. Obviously, having grown up in the 1970s in South Carolina, it’s hard to avoid Son of a Son of a Sailor by Jimmy Buffet. It’s extremely difficult.

That’s not bad, I thought you were working toward Christopher Cross.

No, I’m going to avoid Christopher Cross’s Sailing. Ride Like the Wind or Arthur, but not Sailing. And the Wreck of the Edmund Fitzgerald. And Sloop John B. Actually you know what our sailing song was for two days we were out there and we were just slowly gyring being becalmed. It was Will it Go ‘Round in Circles. We were all singing, “Will it go ’round in circles.”

There was a [competitor in the race] which was to our port and astern, maybe 8 miles. You could barely see its light at night, and during the day it was just this little bump on the horizon. Of course no one’s supposed to turn the prop because the race hasn’t been called yet. We’d look around and go “Holy s&*t, he’s must be turning his prop. Look he’s going ahead of us.” But the boat’s just turning and we have no reference points, perfectly blue sky, not a cloud. Perfectly flat water, so flat you could see the stars by looking down at night. So we realized that we were slowly turning and the compass was staying still, of course, and so Will it Go Round in Circles by Billy Preston become our theme song for the whole thing.

Last question. Is there anything that you’re especially looking forward to with this race?

Spending more than 12 hours in Bermuda would be nice. [In 2005] we arrived at 10:30 p.m. on Saturday night and I had a 10 a.m. flight the next morning. So I literally came in, took a shower, tried to sleep—which was impossible because the room wouldn’t stop spinning—and then I had to get on an airplane the next morning.

Well booking a 65-footer is a good first step.

That was part of the impetus. I’d like to maybe play a round of golf and have a Dark N Stormy.


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