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Although hundreds of prom dresses every year are fashioned after the pop star's style, Madonna never actually went to her 1975 prom at Rochester Hills High School in Michigan. Instead, she claims she "sat home alone. Couldn't get a date." (Photo: Stephen Lovekin/Getty Images))See more Celebs at The Daily Beast
At just 15, Miley Cyrus learned she didn't always get the best of both worlds. When she was high school freshman-age, the "Hannah Montana" star told Maureen McCormick at the Country Music Television Awards red carpet in 2008, "I should be [going to prom], but I'm not… I am shooting my movie during prom days, so I won't be there." Still, Cyrus admitted that at the time, she wasn't really missing out: "I would be like the single loner at the back of the prom… That's the worst! I am not going to do that. That is like the worst. You shouldn't even go." Little did she know, that movie—"The Last Song"—would introduce her to her future boyfriend and co-star Liam Hemsworth. (Photo: (Photo by Kevin Winter/Getty Images)See more Celebs at The Daily Beast
"I didn't go to the prom; I was at military school," the "Wedding Crashers" star admitted in 2006. The actor ended up in the New Mexico Military Institute, after getting expelled from Dallas' St. Marks after just two years for raising hell, but eventually finished his coursework, heading to the University of Texas in Austin in 1987. (Photo: Photo by Dave Hogan/Getty Images)See more Celebs at The Daily Beast
Although hundreds of prom dresses every year are fashioned after the pop star's style, Madonna never actually went to her 1975 prom at Rochester Hills High School in Michigan. Instead, she claims she "sat home alone. Couldn't get a date." (Photo: Stephen Lovekin/Getty Images))See more Celebs at The Daily Beast
Though he's attended many a movie prom—from "Whatever It Takes" to "Never Been Kissed"—actor James Franco did not actually have the chance to go through the ritual in real life. The Palo Alto High School student was indeed a charmer—he earned Best Smile in the school's yearbook-so finding a date was not the issue. "My girlfriend at the time was an actress and my prom was actually on my 18th birthday, but there was also a trip to Aspen, Oregon, to go see the plays. So, we opted to see the plays. We had our own little prom," the actor told Lindzi.com (Photo: Jemal Countess/Getty Images)See more Celebs at The Daily Beast
Comedian Sherri Shepherd may have been able to laugh through a lot, but the now 44-year-old "View" cohost regretted missing out on her prom at Hoffman Estates High School near Chicago. She recently got a second chance two decades later when WWE superstar MVP (who had also never attended his prom), escorted Shepherd to her alma mater's dance. When they entered the affair decades in the making, the DJ turned on MVP's theme song—"I'm Comin'" by the Silkk the Shocker—and the two were essentially the king and queen of the evening. "I feel like we're the black Ken and Barbie," Shepherd admitted. (Photo: Michael Loccisano/Getty Images for The Steve Harvey Foundation))See more Celebs at The Daily Beast
Bristol Palin tried to put on a happy face about her pregnancy while her mother was running for vice president in 2008, but the teen mom missed out on many adolescent opportunities, prom included. Palin told People that she skipped prom for financial reasons when she was pregnant with son Tripp. "I don't have that kind of time. And the dress is, like, $400, and the shoes, hair, makeup—it's way too expensive," she said. Still, she admitted she was disappointed, saying missing out on that opportunity "kind of sucked, to tell you the truth." Though the oldest Palin daughter did graduate from Wasilla High School in May 2009, she also revealed there was baby spit-up on her dress and she was unable to attend her friends' graduation parties (Photo: Bryan Bedder/Getty Images)See more Celebs at The Daily Beast
