When the National Labor Committee reported that sweatshop labor was being used to make the clothing for squeaky clean Kathie Lee Gifford’s Wal-Mart line in 1996, the media went nuts. In response, she addressed the allegations on Live with Regis and Kathie Lee, explaining that she was not involved with the hands-on management of the factories, and went on to become an advocate for laws to protect children against sweat shop conditions. In 1998, she made a guest appearance as herself on The Simpsons‘ annual Halloween episode. Now she gets paid for getting sloshed during the fourth hour of Today while making fun of her co-host, Hoda Kotb. Are the two directly related? Probably not, but we’d suggest that it might have helped her tap her “edgier” side.
The Olsen Twins – “Diatribe of a Mad House Wife”
By 2003, Mary-Kate and Ashley Olsen had proven that they were capable of much more than sharing the role of Michelle Tanner. The twins had already started their own production company, Dualstar, through which they released a slew of straight-to-video movies, and licensed clothes, books, fragrances, magazines, and even a line of dolls, for their clamoring tween fan base. But they weren’t exactly cool in the eyes of anyone over the age of 13. In their appearance on the show, the twins narrate the audiotape version of Marge’s novel, The Harpooned Hart. A year later, they became joint CEO of Dualstar and were well on their way to becoming tabloid stars. Maybe it was the fact that they turned 18. But we’d like to think that this self-effacing cameo didn’t hurt.
Dennis Rodman – “Treehouse of Horror XVI” 2005 was a big year for Dennis Rodman. Aside from his guest spot on The Simpsons, he published his second autobiography, I Should Be Dead By Now (which he promoted by sitting in a coffin); he signed with the American Basketball Association’s Orange County Crush (hoping to be picked back up by the NBA); and he participated in a wife-carrying contest in Finland. In this Halloween episode, Maggie turns him into a head with a pacifier body, and he delivers a PSA on adult illiteracy. It must have charmed reality TV execs, because in the following years he appeared on Celebrity Big Brother and Love Island in the UK, ABC’s The Mole, and most recently, as a contestant on the Celebrity Apprentice. He was the fifth contestant knocked off, and his behavior on the show led family and friends to stage an intervention. That landed him a spot on the third season of Celebrity Rehab with Dr. Drew, followed by a stint on Sober House.
The Dixie Chicks – “Papa Don’t Leech”
In the late ’90s, country music group the Dixie Chicks won the hearts of many Americans with songs like “Wide Open Spaces,” “Cowboy Take Me Away,” and “Long Time Gone.” Then in 2003, 10 days before President Bush invaded Iraq, lead singer Natalie Maines told the crowd at a London performance, “we don’t want this war, this violence, and we’re ashamed that the President of the United States is from Texas.” This inspired some people to boycott the Chicks’ shows and burn their albums, while critically, the Grammys kept on coming. Flash forward to 2008, when they cameo-ed as themselves on an episode of The Simpsons about tax evasion in Springfield. (Lurlene’s deadbeat father sells them one of her songs.) Since then, the band has decided to ditch Maines on vocals, and is currently on tour with the Eagles.
Lance Armstrong – “Mona Leaves-a”
When Lance Armstrong broke off his engagement with Sheryl Crow in 2006, he wasn’t the most popular guy in Hollywood (many reports painted him as a playboy and said it was over her “biological clock”). In September of 2008, the same year that he announced his return to pro cycling and plans for participating in the 2009 Tour de France (“in order to raise awareness of the global cancer burden”), Armstrong guest starred on the episode of The Simpsons in which Homer’s mom (voiced by Glenn Close) dies. Since that appearance, his luck has been pretty good. While he placed 29th in his first big race — Australia’s 11th Tour Down Under — his fans generated so much money for local tourism that the government pledged $4.1 million toward the construction of a center for cancer research. He sired two children with his girlfriend, Anna Hansen, despite undergoing chemotherapy for testicular cancer. He finished the 2009 Tour de France in third place, and plans to return this year on Team Radioshack. He might have made an enemy out of Fozzie Bear, but his silly Simpsons cameo helped smooth things over with us.