Felicity Huffman's Transformation

Spending decades in the entertainment business has certainly taught Felicity Huffman a lot. Throughout her long career, the Bedford, New York-born celebrity has immersed herself extensively in the acting craft, taking her talents to the stage, television, and ultimately, film. Accolades and nominations eventually followed, although things rarely came easily for Huffman. While she has acting credits that go all the way back to the '70s, it took the actress several years to finally break into the business and truly gain the status of a Hollywood star.

Meanwhile, just when it seemed like things were finally looking up for Huffman, the actress became embroiled in a scandal that nearly destroyed everything she worked so hard to earn. Since then, Huffman has been determined to put the past behind her. she has also been on the road to redemption as she sets out to regain her footing in the industry once more. Luckily for her, Hollywood loves a good second act.

Growing up, Felicity Huffman was "loud and obnoxious," at least according to her mother, Grace Ewing Huffman. And that's why she recommended that the young Felicity get into acting, even sending her to an acting camp when she was only 11. While there, she ended up joining the chorus and loved every minute of it. For Huffman at that time, it wasn't so much about the acting lessons they taught at camp. Rather, it was the people around her. "I think I fell in love with the group before the actual activity or art of it," the actress even admitted during her Television Academy Foundation interview.

After going to acting camp, Huffman was hooked. Later on, she also attended the Buckley School in Los Angeles, which boasts a strong performing arts program. In the spring of 2022, the school staged its own production of "Legally Blonde: The Musical."

After getting a little on-screen acting experience, Felicity Huffman became fully invested in pursuing acting as a career. As she got older, she eventually attended the Interlochen Arts Academy in Michigan, which allowed her to do more theater work in high school. Later on, Huffman also studied drama at New York University. Eventually, this led her to become one of the Atlantic Theater Company's founding members. It was also here that she met and fell in love with actor William H. Macy.

The first time they saw each other, however, Huffman and Macy couldn't date. Huffman was enrolled in Macy's acting class and the actor didn't want to date a student no matter how much he was attracted to her. Eventually, it was Huffman who made the first move. When they ended up attending the same house party in Vermont, Huffman invited Macy to check out a barn. That's when the actor decided he had to make his move. "So I screwed up my courage, grabbed her hand and planted a big one on her," Macy recalled during an interview with the The Washington Post.

After doing theater, Felicity Huffman was ready to pursue on-screen roles, and during the early '90s, she booked several of them. For instance, she landed brief guest roles on shows such as "Early Edition," "The X-Files," "Chicago Hope," and "Law & Order." At the same time, Huffman also landed a regular role on Aaron Sorkin's dramedy "Sports Night." The actress believes that she booked the Emmy-winning series because of "Speed-the-Plow." Unfortunately, however, the show only ran for two seasons.

And while the actress managed to book several roles, she also struggled to win over casting directors much of the time. As Huffman recalled in an interview with Entertainment Weekly, one even once told her, "You're so good, but you're just not pretty." 

"They weren't saying it to be mean," Huffman added. "They just didn't want me to think I wasn't right because I couldn't act." At one point, the actress even earned just $12,000 in a single year as she ended up doing several failed pilots. Things got so bad that Huffman started to think about studying at the Marinello Schools of Beauty (the schools have since shut down) and becoming a hairdresser.

Felicity Huffman and William H. Macy also eventually started a family, welcoming their first child, daughter Sophia Grace Macy, on August 1, 2000. From the time that she learned they were expecting, Huffman devoted a lot of time to preparing herself for their baby's arrival, reading as many books, and getting tips from parents who seemingly managed to raise incredible children. Despite this, however, the actress still found herself struggling with parenting the moment her daughter was born. "I did not enter into motherhood with any sense of equanimity or grace," Huffman even once told the Los Angeles Times. "I'm surrounded by women who are much better mothers than I am, and they come to it much more naturally."

Not long after, Macy and Huffman also welcomed their second daughter, Georgia Grace Macy, on March 14, 2002. And for Macy, their youngest daughter reminds him of his wife in a lot of ways. "Georgia is like her mom: fierce," the actor told People. "[S]o smart, like Felicity." Over the years, Huffman juggled family with work, sometimes leaving her daughters with Macy in Los Angeles as she traveled to shoot scenes.  

As Felicity Huffman worked on "Desperate Housewives," she also gravitated toward the film project "Transamerica," which tells the story of a transgender woman named Bree who suddenly discovers that she has a son. When Huffman's agent sent her the script for the low-budget film, she considered taking on the lead role without any hesitation and that's exactly what Duncan Tucker, the film's writer and director, wanted in his lead actress. "If an actress was going to be scared off by the material, then she wasn't the right actress," he told Entertainment Weekly. And while other stars may hesitate to drastically change their appearance for the cameras, Huffman didn't care. "I was never a beauty, so it was never something I had to safeguard," the actress also told the publication.

"Transamerica" went on to score some good critical reviews following its release in 2005. Many also praised Huffman for her performance in the movie, which eventually led to her first Oscar nod. Amid all of this, however, transgender actress Alexandra Billings knew that Huffman's success in the movie could have been hers as she was the one originally cast in the lead. Billings eventually had the opportunity to confront Huffman about it. "[S]he felt really bad, which made me feel great," Billings told Screen Crush.

For some time, things continued to look bright for Felicity Huffman. The actress kept on booking film and television roles, working on the miniseries "When They See Us" and starring in the films "Otherhood" and "Tammy's Always Dying." But then, Huffman's world came crashing down after her involvement in a college admissions scandal came to light.

Federal investigators spent much of 2018 building a case against Huffman and other parents after an unrelated securities fraud investigation led them to discover a long-running scheme to tip college admissions scales in favor of the children any parents who paid their perpetrator, self-proclaimed college counselor Rick Singer, to do so. After Singer met with authorities, he agreed to record all phone calls and meetings with parents who solicited his "services" to get their children's admitted into some of the most prestigious schools in the U.S. Eventually, this led to some famous Hollywood parents, including Huffman and "Full House" actress Lori Loughlin. In an ABC interview, Huffman said the FBI arrested her at her home, waking her daughters up at gunpoint.

Soon after the scandal became public, Huffman pleaded guilty to paying Singer $15,000 to inflate her elder daughter's entrance exam scores and buy her more exam time. Months later, Huffman was sentenced to 14 days in prison. On October 15, 2019, the actress reported to prison where she remained for 11 days. She also had to fulfill 250 hours of community service.