When David Friend, a Vanity Fair editor, embarked on writing The Naughty Nineties: The Triumph of the American Libido (Twelve Books), he knew that chronicling a decade through the prism of sex would take him across the country—from Sausalito, California, where he witnessed a demonstration of “orgasmic meditation,” to the notorious sex scandals at the highest levels of politics in Washington D.C.

But to fully make sense of the decade that gave us the Brazilian bikini wax, the Pamela Anderson-Tommy Lee sex tape, The Vagina Monologues, Viagra, and Girls Gone Wild, he knew he would need some perspective from some folks back home in Chicago.

“I have deep roots there,” Friend said in a phone interview. “My father was a Chicago attorney for many years and my mother was the first female draftsman in Chicago after the war. I grew up in Highland Park. So some of the people I wanted to interview or reference would logically be from my home turf.”

These notable Chicagoans memorably dot the landscape of The Naughty Nineties. Here are Friend’s reflections:

Scott Turow, Michael Jordan, Scottie Pippin, and the “Bro Hug”

“Male power was perceived [in the ‘90s] to be at risk. This was a big deal. You had men going to sweat lodges, participating in the Million Man March, or gathering in stadiums under the umbrella of the Promise Keepers. This was a good thing that forced them to get more in touch with their more balanced inner lives.

"I knew Scott growing up, and we both went to Amherst. One day, he called and said he was noticing that men were hugging and what was that about? He wrote a piece about it for Vanity Fair that referenced the 1997 NBA Finals game in which Michael Jordan, battling a hundred-plus-degree fever, scored 38 points and collapsed into Scottie Pippin’s arms at game’s end. Men’s relationships with other men had crossed the Rubicon into closeness, and that needed to be acknowledged physically.”

Sammy Sosa

"In 1998, Sammy Sosa and Mark McGwire were in this great home run race [to surpass Roger Maris’ 61 home runs in a season], and the entire nation was following it. My son, Sam, was raised in New York, but is a Chicago Cubs fan as am I and as was my father and grandfather. He was 10 at the time and I took him to a photo shoot at Wrigley Field to photograph Sammy. It was a wonderful morning and there was this naiveté that we had this great home run race with these two titans.

"By the end of it, McGwire confessed he had taken artificial enhancements to bulk himself up. Sosa never admitted it. It’s one of the great asterisks in sports records. Sam is now a 28 year-old jazz musician. His takeaway is that it was still a beautiful thing, but that sometimes you have to wonder about the extent to which as a culture we’re trying to get an edge all the time. The 1990s was ‘the Amplified Age.’ Between Viagra for men and breast implants for women, we were trying to work the angles.”


“She was a key figure [in the decade]. For all the things she is—talk show host, producer, actor, philanthropist, producer, network entrepreneur—she was our mother confessor. The Oprah Winfrey Show, through Oprah’s acknowledgement of her own struggles, was able to draw out from people their own foibles. Every day on television, people were much more open about [sharing] the issues they were going through; redemption through revelation. In the growing confessional culture, she was seminal in that regard.”

Jesse Jackson

“The Rev. Jesse Jackson kindly agreed to sit down and talk about the Million Man March. It was his view that Dr. Martin Luther King’s March on Washington [in 1963] was about civil rights, changing laws, and asserting one’s entitlements and rights as an African-American man or woman. Then came the ‘90s, and the Million Man March, which was not a civil rights march, but, according to Rev. Jackson, was about personal values and empowerment, and how black men and men of color were going to take responsibility for who they were.”