© Courtesy Comedy Central

"I may not know much about sailing, but I know I can beat you to Bermuda."

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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?