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Stephen Colbert Featured in Sailing World Magazine.

Sailing World Magazine interviews Stephen Colbert.

Stephen Colbert Challenges You to an Ocean Race.

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.

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