Between the Lines, Online: Boxers or Briefs?

Back in 1992, I took a part-time gig with MTV, analyzing politics on camera and helping produce the network's town meetings with politicians. My job was to work with Tabitha Soren, the MTV anchor, devising some fresh questions. She was a natural and effective interviewer whose youth and rock-and-roll vibe let her slip in more curve balls than her stuffier counterparts on the broadcast networks. Our aim was to make every question from Tabitha and the kids in the audience count.

The first "Rock the Vote" town meeting with Gov. Bill Clinton, assembled on a sound stage in Hollywood, was a ratings smash. Clinton was then running third in the polls behind President George H.W. Bush and Ross Perot and the appearance helped jump-start his campaign, particularly with young voters. It was also endlessly dissected by the media as the fusion of entertainment and politics.

At the end of the program, we launched what we called the "rapid round." In the rehearsal beforehand, we requested that kids pose very short questions to Clinton. On the show, one asked whom he would appoint to the Supreme Court if elected. When Clinton answered "Mario Cuomo" (who later turned down the appointment), it made news. Bush also submitted to an interview with Tabitha, from the back of a train, but he was testy that day and he wouldn't answer questions from kids, which hurt his campaign.

Around this time, I went skiing in Aspen, Colo., with my brother and a couple of his friends. I mentioned to Terry McDonnell (now managing editor of Sports Illustrated) where I was going and he asked a favor. Dr. Hunter S. Thompson owed his friend Terry a piece about Jack Nicholson, who also had a place in Aspen. Thompson was months late delivering the Nicholson story for Terry's magazine. Would I make contact with the good doctor and remind him that Terry wanted the article? Having missed the glory days of Rolling Stone, when Jann Wenner was famous for hunting down Hunter for copy, I happily obliged.

Like every other political writer of my generation, I adored "Fear and Loathing on the Campaign Trail," though I knew Thompson only slightly. When I was profiling Garry Trudeau for NEWSWEEK in 1990, he had raged at me one night for two hours about how the cartoonist had ripped him off for his Uncle Duke character in "Doonesbury." I argued it was homage; he called it theft.

This time, Thompson agreed to meet me at the Woody Creek Tavern, the place outside of Aspen that he made famous as his second home. My brother, his friends and I arrived around 7 p.m., expecting to have dinner with the great man per our arrangement. He showed up, not surprisingly, around 11 p.m., in precisely the manic state we had hoped for, retreating every half hour or so to the men's room for apparent self-medication before resuming his exhilarating rant, which if I remember correctly through the tequila haze had something to do with the decline of sports. The Nicholson piece was quickly brushed off and forgotten.

At a certain point, Thompson had had enough of us and retreated to the bar.

Suddenly, one of my brother's friends, a Chicago commodities trader and no stranger to debauchery himself, loudly re-approached.

"Hunter," he slurred. "I have one more question."

A look of considerable irritation flashed across the legend's face as we recalled his fondness for firearms.

"Boxers or briefs?"

Thompson refused to answer this novel query but whispered something to the barkeeper, presumably about harassment by fans, and the next thing I knew we were staggering around in the snow, tossed out of a tavern by Hunter S. Thompson for being too rowdy.

I must admit, I had never before heard the "boxers or briefs?" conundrum and proceeded to dine out on the story for many months. I saw Thompson a couple more times--once, strangely, when we had breakfast in Little Rock, Ark., and he asked if I'd mind if his beautiful female sidekick "took notes" by videotaping me. I didn't mention the Woody Creek incident to him but among those with whom I shared it was Tabitha Soren, who found it amusing.

After the success of the town meeting during the campaign, Tabitha had more access to the new president than any other journalist. She interviewed him in the Oval Office and Clinton held a second MTV town meeting in 1993, then a third in 1994, which would prove, for obvious reasons, to be his last.

Tabitha always had an easy way with the young studio audience, and during rehearsals for that final forum she introduced the high school and college-age students to the concept of the "rapid round." She suggested they ask anything they wanted of the president, as long as the questions were short. Then, she jokingly threw out a few possibilities, from "What's your favorite album?" to--yup--"Boxers or briefs?"

A 17-year-old in the audience, Laetitia Thompson (no relation), popped the historic question and President Clinton, after expressing momentary surprise, answered: "Usually briefs."

Long before Monica Lewinsky, this was seized upon by commentators as symbolic of everything Clinton did to degrade and embarrass the American presidency. When George W. Bush was elected in 2000 by promising to "restore honor and dignity to the office of president of the United States," he was tapping into perceptions of Clinton that began with him discussing his underwear on national television.

Hunter Thompson ran hot and cold on Clinton, though he liked him far better than Nixon, Reagan or the Bushes. For all of his brilliant eviscerations of politicians (Hubert Humphrey was "a rat in heat"), the most enduring began with a question that even he would not answer.

For a writer, that's painful, and I never had the heart to tell him.