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What has Ananda Lewis been up to since Woodstock ’99?

Bruno Cooke August 4, 2022
Celebrities Visit Hallmark's "Home & Family"
Photo by Paul Archuleta/Getty Images


Former MTV veejay Ananda Lewis features in Netflix’s new three-part series about Woodstock ’99, which as the docuseries’ title suggests went less than swimmingly.

Lewis appears as a talking head in the first episode, titled How The F**k Did This Happen. It arrived on the streaming platform yesterday (Wednesday, August 4, 2022).

She will turn 50 next year, but several Netflix viewers have commented on Twitter and elsewhere that she looks younger than she is. 

Was Ananda Lewis personally involved in Woodstock ’99, what was she doing and how old was she at the time, and what has she been up to since?

Photo by Jeff Kravitz/FilmMagic, Inc

Ananda Lewis on Woodstock ’99: ‘It was a perfect storm’

“That summer of ’99,” Lewis explains early in the documentary episodes, “we were doing Isle Of MTV, and that was in Nassau, Bahamas, Paradise Island.”

“MTV said ‘we’re going to send you back to New York for Woodstock ’99’, and I was like, ‘back to New York?!’”

“But it was going to be the biggest party on the planet. … Three days of incredible music and nonstop partying. This was massive.”

As numerous other talking heads including late festival co-founder Michael Lang and performer Jewel Kilcher explain, several factors meant that Woodstock ’99 didn’t go as smoothly as it might have done. Ananda Lewis, for one, describes it as a “perfect storm.”

Meanwhile, one thing that has stuck out for several viewers is how good Ananda looks now, more than two decades later.

How old was she at the time?

When MTV flew her from the Bahamas to New York to cover Woodstock ’99, Ananda Lewis was 26 years old.

Born March 21, 1973, in Los Angeles, she’s of African American and Native American descent. Specifically, she has connections to the Muskogee Creek and Blackfoot tribes. Her first name means “bliss” in Sanskrit.

From an early age, Ananda Lewis struggled with a speech impediment. She stuttered until she was eight years old, but appears to have moved through it before hitting double digits.

Photo by Evan Agostini/Liaison

In 1981, when she was eight, she entered herself in the Little Miss San Diego Contest, a beauty contest. She won with a self-choreographed dance routine set to Stevie Wonder and Paul McCartney’s Ebony And Ivory.

What has Ananda Lewis been up to since Woodstock ’99?

Lewis majored in history at Howard University in Washington DC, graduating in 1995. She found her way into the world of television hosting via a role in Black Entertainment Television’s Teen Summit in 1996.

While at MTV, she went from interviewing rappers to hosting topical programs such as two MTV forums on violence in schools. She made headlines when she announced in 1998 that she would be celibate for at least six months, and led tributes for the singer Aaliyah after she died in a plane crash in 2001 – they had been friends.

MTV VJ Ananda Lewis arrives at Cosmopolitan’s 5th Annual ‘Fun, Fearless Females of the Year’ luncheon at the Metropolitan Pavilion in New York City. 01/29/2001. Photo: Evan Agostini/Getty Images.

She got her own show in 2001, but it was ill-fated. It debuted on September 10, 2001, a day before the attacks on the World Trade Centers. It lasted just one season.

But in 2004, Ananda became The Insider’s chief correspondent on celebrity subjects. In the year that followed, she interviewed Paris Hilton, Don Cheadle, Ryan Phillippe and Dyan Cannon. 

In 2011, Lewis gave birth to her first son, Langston. Her husband, and Langston’s father, is Harry Smith.

In 2020 she revealed that she had been battling breast cancer for two years

On October 2, 2020, Ananda Lewis posted a nearly seven-minute video to her Instagram followers, in which she shared that she had been battling breast cancer for the last two years.

Trainwreck: Woodstock ’99 | Official Trailer | Netflix

Trainwreck: Woodstock ’99 | Official Trailer | Netflix

“For a really long time, I have refused mammograms,” she says in the video. “And that was a mistake.” She took the opportunity to urge her followers to “get your mammograms.”

“If I had done the mammograms from the time they were recommended, when I turned 40, they would have caught the tumor in my breast years before I caught it through my own breast exam – self exam – and thermography. … What I’m dealing with is stage 3 breast cancer that is in my lymphs. I need you to get your mammograms.”

She continues to be active as a public figure. In recent years, Lewis has been a spokesperson for the Humane Society and literacy nonprofit Reading Is Fundamental. Find links to her merchandise here, including items from her Protest collection, and supplements. 

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Bruno is a novelist, amateur screenwriter and journalist with interests in digital media, storytelling, film and politics. He’s lived in France, China, Sri Lanka and the Philippines, but returned to the UK for a degree (and because of the pandemic) in 2020. His articles have appeared in Groundviews, Forge Press and The Friday Poem, and most are readable on Medium or