The Stunning Transformation Of Cybill Shepherd

Born in 1950 in Memphis, Tennessee, Cybill Shepherd never imagined she'd enjoy a wildly successful Hollywood career that has spanned six decades and counting. Yet that's precisely what happened, sending her on a showbiz journey as a sought-after actor in film, television, and stage. She's received plenty of accolades along the way, appearing in Oscar-winning movies, receiving multiple Emmy nominations, and winning four Golden Globes. Through it all, Shepherd also carved our a parallel career as a singer. "I started at the top and have been working my way down ever since," she jokingly told the Las Vegas Journal-Review of the trajectory of her career.

In addition to her impressive roster of screen credits, Cybill Shepherd made a splash with her past relationships, from her scandalous relationship with director Peter Bogdanovich to an affair with co-star Jeff Bridges — never mind her torrid fling with the King himself, Elvis Presley. It's been an amazing journey, and it's far from over. 

As Cybill Shepherd wrote in her biography for her website, her earliest inclinations toward entertaining arrived at the age of 5, when she and her sister sang along with Elvis Presley's "Blue Suede Shoes." She continued singing throughout her childhood, and her talent shone through. At 9 years old, she auditioned for her church's choir and became a featured soloist. "My formal training began, at sixteen, studying with the coach of the Metropolitan Opera Chorus when the company was in my home town [of] Memphis, Tennessee," Shepherd wrote.

She began to pursue music more seriously when she formed her own folk group, Cybill and Friends. Modeled after popular folk trio Peter, Paul and Mary, her group began earning money by performing at parties, which paid as much as $50 per gig. "To my shock and amazement, we weren't even runners up at the East High School talent show," she recalled.

In the decades that have passed since then, singing has remained a touchstone for Shepherd. In addition to recording several albums, she's also headlined cabaret-style musical revues. "Music is my first love," she wrote.

As a teenager growing up in Memphis, Cybill Shepherd's charismatic personality, musical talent, and striking beauty made her a natural for beauty pageants, which were at the zenith of popularity when she was a teenager in the 1960s. In 1966, she competed in the Miss Memphis pageant and wound up winning. "For my talent portion I sang 'Don't Think Twice It's All Right' accompanying myself on the ukulele," she wrote in her online bio. 

Shepherd went on to compete in a national pageant, representing her hometown as Miss Memphis. She wasn't nearly as successful in that competition but was awarded the title of Miss Congeniality. Interviewed by the Memphis Commercial Appeal, Shepherd looked back at her brief pageant career, opining that she "didn't even make the finals." She continued, saying, "I still have that [Miss Congeniality] award, it's pretty ugly, I put it down in the office with all my ugly awards."

In addition to singing and pageants, teenage Cybill Shepherd had also been doing some modeling, appearing in local advertisements courtesy of a Memphis photographer she knew. When she was 17, a modeling agency on a scouting trip to Memphis took some photos of her. Those photos were impressive enough that she was invited to New York. She consulted her parents, and they all jointly agreed that she'd be better served to finish high school first. 

Eventually, she did make it to New York and was invited to compete in the Model of the Year pageant. She was named the winner, and her modeling career exploded. She became a "Breck girl," serving as the centerpiece of advertising campaigns for Breck shampoo, as well as the face of CoverGirl. Shepherd also ventured beyond posing for photos when she was cast in her first TV commercial, extolling the virtues of a brand of toothpaste.

By the early 1970s, Shepherd had become ubiquitous in fashion magazines, a true supermodel before that term was even popularized. It was at that high point in her modeling career that one of her magazine covers would go on to steer her life in an unexpected new direction.  

Few would have guessed that Cybill Shepherd would become an actor — including Shepherd herself. "I had no interest in being an actor, whatsoever," Shepherd admitted in an interview with the Television Academy. That all changed when film director Peter Bogdanovich and his then-wife, producer Polly Platt, were in a supermarket checkout line and spotted Shepherd on a magazine cover. At the time, they were in the process of casting his upcoming movie, "The Last Picture Show," but were having difficulties finding the right actor to play the female lead, Jacy Farrow. "She looked like she had a sexual chip on her shoulder, as if she were daring you to try something," Platt recalled in an interview for the book "Easy Riders, Raging Bulls."

Suddenly, a pageant queen-turned-model, whose only acting experience consisted of smiling in TV commercials, was cast as a lead in a movie. As Shepherd recalled when interviewed for the PBS documentary about her co-star in the film, actor Jeff Bridges, she was starting from scratch. "I was much more of an abject beginner than Jeff," she said. "He'd done one film before. ... And I never acted before." The film ultimately received eight Oscar nominations, winning two.

Thanks to the critical and commercial success of "The Last Picture Show," Cybill Shepherd became a hot commodity in Hollywood. She'd also entered into a romantic relationship with that film's director, Peter Bogdanovich, which broke up his marriage. More movie offers poured in, and she had star billing for her second-ever movie, starring opposite Charles Grodin in the comedy "The Heartbreak Kid." She then starred in "Daisy Miller," a period comedy set in the late 1800s, before starring alongside 1970s box-office king Burt Reynolds in the Bogdanovich-directed 1975 musical comedy "At Long Last Love" and taking a small role in Martin Scorsese's acclaimed "Taxi Driver," which came out the following year. 

At the same time that her acting career boomed, Shepherd also continued to tap into her modeling background for increasingly lucrative advertising work. This included her becoming the "Kodak Girl," featured in the film manufacturer's various advertisements.

As for her relationship with the director, it came to an end, both personally and professionally, long before Bogdanovich's death in 2022. In fact, it came just after "At Long Last Love" was savaged by film critics. "It seems to designed as a showcase for Cybill Shepherd's musical-comedy talents, and she's a hopeless amateur," wrote Pauline Kael in her review for The New Yorker. Shepherd, who considered herself to be more of a singer than an actor, was understandably miffed. "To my shock and embarrassment one review said, 'Cybill Shepherd cannot walk, talk, much less sing.' He was right about the walking and talking part, but I actually sang pretty well considering it was all done live without overdubs," she wrote in her bio.

Cybill Shepherd was deeply impacted by the negative reception to "At Long Last Love." She responded by returning to Memphis. Not only was she seeking the comfort of home and family, she was also following advice that she received from legendary actor and director Orson Welles on how she could improve herself as an actor. "He said, 'Do theater anywhere but L.A. and New York," Shepherd told the Television Academy. 

She began performing in what used to be known as the "straw hat circuit," similar to summer stock. Shepherd starred in traveling productions, performing the same play in city after city. "You learn to be not selfish, is my experience," she explained. Those plays included a run in "Lunch Hour" with "Hawaii Five-O" star James MacArthur.

As Welles predicted, Shepherd's experience in regional theater was a transformative one. "That's when I really came alive as an actress and a singer," she told People in 1985, "but I was barely breaking even financially." In 1982, she was urged to return to Hollywood when her former agent, Sue Mengers, offered a blunt assessment of her career. "Cybill, you've been in Memphis for four years. You might as well be dead," Shepherd recalled Mengers telling her.

Relocating from Memphis to Hollywood was just the beginning of Cybill Shepherd's comeback attempt. Once starring in big-budget Hollywood films, she now found herself relegated to guest spots in TV shows such as "Fantasy Island." Her cache rose in 1983 with a starring role TV series "The Yellow Rose," but comeback hopes were quashed when the show was canceled after its first season. 

In 1985, Shepherd was cast opposite then-unknown actor Bruce Willis in "Moonlighting." In the crime-solving rom-com, Shepherd played former model Maddie Hayes, who hires Willis' character, David Addison, to work with her at her detective agency. The show proved to be a hit with viewers, who couldn't get enough of the characters' will-they, won't-they relationship. The show led Cybill to win two Golden Globes, in addition to two Emmy nominations. 

As the show's ratings soared, tabloid reports detailed a bitter feud between Shepherd and Willis. As it turned out, the tabloids were right on the money. "Yes, Bruce Willis and Cybill Shepherd hated each other," "Moonlighting" co-star Curtis Armstrong wrote in the 2017 book, "Revenge of the Nerd" (via NPR). Confirmation also came from Shepherd, although she insisted the behind-the-scenes rancor was a form of method acting. "Yes, we had fights all the time," Shepherd told the Television Academy. "That was part of the preparation ... so it was real." Ultimately, Shepherd has come to see the series as her professional high point in her career.  As she told she told Palm Springs Life, "If I had to choose one [highlight of my career], it'd probably be 'Moonlighting.'"

After "Moonlighting" ended in 1989, Cybill Shepherd focused on her music career while also appearing in several movies — mainly of the made-for-TV kind. In 1995, she was tapped for "Cybill," her first-ever TV sitcom. In this series, Shepherd starred as Cybill Sheridan, a successful actor and single mom raising two kids from different ex-husbands, whose career was in full decline during middle age. As she told the Television Academy, the premise intrigued her. "I love the idea of a woman who has two ex-husbands and children by two husbands, and the craziness of that," she said.

Lightning struck again, and Shepherd had another hit on her hands with "Cybill" — along with two more Golden Globe wins and three more Emmy nominations. "It was incredibly fun," said Shepherd of her sitcom experience, which ended in 1998 when the show was abruptly canceled after four seasons. 

Years later, Shepherd made a shocking claim about the cancellation of her sitcom. Appearing on Sirius XM's "The Michelle Collins Show" in 2018, she declared, "My show could've run another five years, but I didn't fall on the right side of Les," she said, referring to then-CEO of CBS Les Moonves, now-husband of Julie Chen. According to Shepherd, Moonves, who was married to Nancy Wiesenfeld at the time, invited her to a meal and then proceeded to put the moves on her. When she rebuffed him, he retaliated by canceling her show. Shepherd's claim lines up with the multiple allegations of sexual misconduct that resulted in Moonves' firing in 2018.

With time on her hands after the cancellation of "Cybill," Cybill Shepherd decided to tell the story of her life. The result is her 2000 memoir, "Cybill Disobedience," which boasted the ungainly (albeit intriguing) subtitle, "How I Survived Beauty Pageants, Elvis, Sex, Bruce Willis, Lies, Marriage, Motherhood, Hollywood, and the Irrepressible Urge to Say What I Think." For Shepherd, the motivation for writing the book wasn't just financial, but it also presented the opportunity to set the records straight. "Certain stories had to be told, what I've been through to become who I am now," she explained in an interview with the Sunday Times (via Mary Ellen Mark).

In September 2000, Shepherd took on another challenge when she was hired to host "Men Are from Mars, Women Are from Venus," a relationship-based syndicated talk show inspired by the bestselling book of the same name. As a source told Broadcasting & Cable, it was the format that was the real star of the show, not its host. "This isn't the Cybill Shepherd show," the source said. "The show isn't solely dependent on her as talent. This is a format-driven show where someone is carrying the format."

Shepherd didn't last long as host. Just a few months after the series' debut, she was replaced by five other hosts. Columbia TriStar Production president Russ Krasnoff told Broadcasting & Cable that the studio and Shepherd had "an adult parting of the ways." Krasnoff also told People that Shepherd was axed because she was "not providing both sensibilities of men and women" (via ABC News).

With her brief and disastrous foray into the realm of talk shows in the rearview mirror, Cybill Shepherd returned to acting. She landed her biggest role in years when she was cast as domestic diva Martha Stewart in the TV movie "Martha Inc.: The Story of Martha Stewart."  "I had to learn how to chop food without looking, [while] looking at the camera," Shepherd told the Television Academy of the preparation she undertook to play Stewart.

Two years later, Shepherd portrayed Stewart a second time in the 2005 follow-up movie, "Martha Behind Bars." This time, the focus was on the months Stewart spent in prison after being convicted of insider stock trading. "I have more admiration for her than ever before after doing the second movie," Shepherd told the New York Post. "This woman's been through a hell of a lot."

Stewart herself was thoroughly unimpressed with Shepherd's portrayal. While Charles Grodin guested on Stewart's daytime talk show, the conversation turned to Shepherd, his former co-star in "The Heartbreak Kid." When Grodin pointed out that Shepherd had played Stewart, the host declared, "Very badly ... and why she would ever do that, I would never know."

Cybill Shepherd was able to draw on the experience she'd accrued from her earlier stage work when she made her Broadway debut in "The Best Man," written by Gore Vidal. Shepherd was part of an ensemble cast that also included "Full House" cast member John Stamos, "Sex and the City" star Kristin Davis, John Larroquette of "Night Court" fame, and veteran actors James Earl Jones and Angela Lansbury. 

"When I first would come on the stage, there was such an enormous response from the audience, which was thrilling," Shepherd told the Television Academy of being on Broadway for the first time. "And I always felt a little bit like I'd failed, because I never quite had that response [at the end of the play]. Of course, they sat there so long, through two intermissions."

Shepherd wound up exiting the show unexpectedly when, just a week before the end of the play's run, she was forced to drop out when her mother became ill.

When Cybill Shepherd returned to Memphis following the poor reception of ""At Long Last Love," she quickly fell into a romance with David M. Ford, a local auto parts dealer. When she became pregnant, they got married. The two ended up divorcing in 1982, amicably, after four years of marriage. 

Shepherd went on to marry chiropractor Bruce Oppenheim in 1987, and the couple welcomed twins prior to their divorce in 1989. Speaking with Fame magazine, Shepherd revealed her second divorce wasn't nearly as friendly as her first had been. "I'm hoping that at some point I'll be able to talk to him and he'll be able to get over his anger about the divorce to be able to talk about what's best for the children," Shepherd said (via Deseret News). 

Shepherd found love again, getting engaged to psychologist Andrei Nikolajevic in 2012. However, they broke off the engagement and parted ways in 2015. "I don't know if I've accrued more than my fair share of lost loves, but I'm something of a haunted person from the damage," she wrote in her memoir, "Cybill Disobedience."

You may be wondering whatever happened to Cybill Shepherd. While she is into her seventh decade of life and has, of course, slowed down, she's continued to take on acting work. In 2021, she appeared on the TV series "Guilty Party" and starred in the television movie "How to Murder Your Husband." In 2024, Shepherd was honored for her contribution to comedy, receiving the Comedy Hall of Fame Award from the Palm Springs International Comedy Festival (PSICF). "I don't think people realize how much Cybill Shepherd has given us in terms of comedy," said PSICF president Paul Cruz in a statement to the Palm Springs Tribune. "Since the beginning of her film career, comedy has always been there, and we are so very excited to celebrate her for all her great work."

That honor held special significance for Shepherd. "I couldn't believe I'd actually won an award, because I was nominated four times for the 'Cybill' show but never won," she told Palm Springs Life of other award nominations. "Comedy is everything to me," she told Us Weekly of being honored by the PSICF. "It's great to be getting a Comedy Award."