Last month we gave the heads up that Stephen Colbert was to be on the cover of the May 2011 issue of “Outside” Magazine. We loved the preview of the cover and now that the issue is out we get the whole story of his fateful voyage from Charleston, SC to Hamilton, Bermuda in the 2005 Charleston Bermuda Race . It’s scary stuff…
Stephen Colbert’s (Shocking!) Secrets of The (Very!) Extreme
For God’s sake, pump out your head! And that’s just the first thing I learned on my wild ride into the Bermuda Triangle.
By Stephen Colbert….
There comes a time in every man’s life when he must ask himself, “What can I endure? Of what mettle am I made?” This was not one of those times. I thought this would be a booze cruise to Bermuda.
So on a Sunday in late May 2005, I boarded the Tao, a 45-foot double-masted wishbone-rigged ketch (I don’t know what a lot of those words mean), unsure how my life preserver worked, unclear on the difference between a sail and a sheet, the only knot I could tie a Windsor. We cast off, and the boat’s owner, Paul Dorn, steered our eight-member crew into the harbor. Then rang the gun! Up came the wind! The sea called! Next stop, Bermuda!
Our mainsail started tearing immediately. It was new, had never been hoisted before, and was a poor fit. I got a quick lesson in making radial stitches on a 50-foot sail loaded with wind. Using a steel palm thimble and a pair of pliers, Eric Walker, a veteran sailor from Charleston, and I drove a six-inch needle through sailcloth stiff as rawhide. If you missed with the thimble, the needle would go through your hand. My pleasure cruise had quickly devolved into a Neolithic sewing circle. But the sail was saved, we passed Fort Sumter, and the land receded over the horizon and into memory. Ahead lay 777 nautical miles of ocean.
We divided into two watches, portside and starboard, taking turns manning the helm. For the next seven days, we would sleep, at most, four hours at a stretch—basically the same pattern Stalin used to break his enemies.
That first afternoon at sea, our power inverter blew out, meaning we couldn’t charge our weather station, computers, or satellite phone. It also meant that none of us could jack our iPods into the stereo and crank up our carefully crafted nautical playlists. While this was a disappointment, it may have saved us from a lethal cocktail of Gordon Lightfoot, Christopher Cross, and Jimmy Buffett.
On day three, as we bobbed along in windless conditions, we lost both our toilets. Boat toilets, or “heads,” are floating Porta-Potties. Ours, through an understandable oversight, had not been emptied since the Carter administration. We tried opening a relief valve (provocatively called an “ocean cock”)—no go. It had to be pumped out by hand. As a father of three, I was used to dealing with other people’s waste, so I volunteered, as did two other crewmembers. We took turns using a hand bilge pump to siphon the blue-water slurry into five-gallon paint buckets. After an hour or so, it was getting harder and harder to see out of my glasses. Turned out the gasket at the top of the pump had a poor seal; with every pump, a fine blue mist of aerosolized dook water sprayed into the confined cabin. I dropped the pump and scrambled topside for fresh air, my one great fear of this adventure suddenly vanished. I now knew that I would not drown. I would die from amoebic dysentery.
…
To calm our nerves as we contemplate Stephen heading into the Bermuda Triangle once again in a couple of weeks, the kind folks at OutsideOnline.com have also posted a video of the photo shoot!
[NB: it seems to be on an infinite loop, which is not necessarily a bad thing]

Holy cannoli. *shakes head* That is some story. But the fact that despite all the crazy s*** he and the crew went through (on top of losing the race), he still wants to go through that experience again for the pure joy of being in the middle of a clear blue “horizonless” nowhere with good friends is (somewhat) something we can all relate to. I think (I know I personally have) we all have had times when we’re doing something we love and we keep coming up against problem after problem, obstacle after obstacle, to the point when we’re completely fed up and want to give up. But at the end, when we sit down and think about it, we remember that we do the things we love BECAUSE we love them, no matter what hardships we go through, and so our conviction to keep on doing them is renewed and sustained. And I think that this is exactly how Stephen feels about sailing…although being honourary “Morale Officer” and captaining a 65-foot racing yacht has to be a pretty nice leg-up from what he did back in 2005. I’m happy how he manages to do things he really loves in his crazy busy schedule. I’ll certainly be praying that he has a safe and (relatively) uneventful trip and for him to have the time of his life.
ReCaptcha: riveree strategies. First of all, this ain’t no river he’ll be crossin’ in a couple of weeks, and secondly, I’m sure he’ll have plenty of strategies this time to make sure things go smooth…as well as to win (in ways only “Stephen Colbert” would do). :P
Shout Out (Hey!):
+3
P.S. Stephen looked so funny trying to get into the refrigerator in the photo shoot clip. What wouldn’t I give to help him with dress and make up. And what he did when posing with that popsicle? Mmm…
Shout Out (Hey!):
+2
Thanks so much for this! I would say poor Stephen, but after reading that last paragraph, he seems to remember the trip quite fondly, which is so very sweet. But still. That trip is definitely a fine example of Murphy’s Law!
The thing I liked most about the article is that Stephen wrote it. It really showcases what an unbelievable writer he is, weaving clever jokes throughout the wonderful imagery. This is another reason why I would love for him to write a book of autobiographical essays out of character.
Difference makers:
+8
Yes, Lockhart!
As I read the article I was thinking how smooth, lyrical, poignant, and funny his writing is.
I sincerely hope he writes a book out of character someday, too. This ‘honest’ piece is something wonderful.
Shout Out (Hey!):
+4
He has to write a book about his life, out of character. I am going to demand it. Maybe not now, maybe after the show ends and he has time to reflect over his career, but a bigger glimpse into his life is due.
Shout Out (Hey!):
+3
Ok. He just won life with “aerosolized dook water.” You have my sword, sir. And my axe. AND my bow.
Difference makers:
+7
“The only knot I could tie a Windsor…” Snicker.
Seriously, he is such a lovely writer. This is a pleasure to read on many levels.
Wishing you a happy, easy, and winning sail, Sir Stephen.
Shout Out (Hey!):
+3
He is a simply lovely writer. Echoing what others have said, he could write such a fantastic autobiography someday. God only knows he has the life experiences (molding The Daily Show! creating his own show! winning Emmys! meeting celebrities! running for President! becoming the greatest satirist of his generation!), not to mention the natural writing ability. So Stephen, if you’re reading this… When the Report is over (gulp), and your kids are grown, and you’re looking for a project… An autobiography could be an amazing one.
Difference makers:
+9
While my true hope is for one out of character, I’d even take a book of essays IN character, now that I think about it. I’m sure Stephen can make up some great stories of “Stephen’s” college days at Dartmouth. Hell, he could put some real stories in there, to keep us guessing. I guess I just want to read anything he writes ’cause he’s so good at it.
Shout Out (Hey!):
+4
Oh, my gosh.
Just when I thought that Stephen couldn’t be anymore awesome.
I hope he has lots of luck on his next trip.
Shout Out (Hey!):
+4
As a writer myself, I am impressed by how well Stephen’s article flows. He really does have writing talent.
I can’t decide if the captain of that boat was incredibly unlucky or incompetent! Certainly somebody should have done a better job of double-checking the equipment. But, fortunately, it sounds like the crew were all great sports about it.
Shout Out (Hey!):
+3
I am so glad that SC gets to have another adventure at sea. I hope he gets a chance to just be a regular guy having a great time, and hopefully a few things will go wrong just to keep the trip memorable (but not as memorable as the last time, thank you.)
Shout Out (Hey!):
+2
What an amazing writer he is. I had read this before when the magazine first came out on the stands, but I just had to read it again, and it gets better with every reading. It seems to me that the only thing as limitless as the horizon Stephen describes, is that man’s talent.
How can someone feel so deeply, write so well, and be so much fun all at the same time?
Shout Out (Hey!):
+1