The Truth About Bailee Madison Is Tumbling Out

There aren't too many actors in Hollywood that can boast a string of more than 50 screen credits extending back for nearly two decades — and not yet celebrated their 25th birthday, that is. 

Bailee Madison is that rare star, having enjoyed phenomenal success as a child actor; she landed her first movie role at age 3 and was just 9 years old when she starred opposite "Dawson's Creek" alum Katie Holmes in "Don't Be Afraid of the Dark." Since then, she's made her mark on both the big and small screens, starring in the short-lived ABC sitcom "Trophy Wife," in addition to spending several seasons in the beloved Hallmark series "Good Witch." She's also pulled off the delicate balancing act required to graduate from kid roles to teen parts and then to adult roles; most recently, she's starred in "Pretty Little Liars: Summer School," in a role that's a definite departure from the kind of wholesome projects for which she's previously been best known.

Despite all those film and TV roles, she's also delved into other areas beyond acting, and every indication is that she's only scratched the surface of what she'll eventually accomplish in what promises to be a successful and enduring Hollywood career. Keep reading to discover more about this intriguing star as the truth about Bailee Madison unfolds.

Bailee Madison was born in 1999 in Fort Lauderdale, Florida. The youngest of seven kids, Madison's mother was an actor who appeared in local TV commercials. As Madison explained in an interview with Story & Rain, her mother would often bring her along when auditioning — and would suggest her daughter if a commercial required a baby. "I think I did my first one at like two weeks old," Madison recalled. "It was a Home Depot or Office Depot commercial, I don't remember."

Like their mom, Madison's older sister Kaitlin Riley (now Kaitlin Vilasuso) was also an actor whose credits include playing the younger version of Charlize Theron's character in the film "Monster." As it happened, Madison was tagging along when her sister auditioned for a role in "Lonely Hearts," a major Hollywood production with an A-list cast that included John Travolta, James Gandolfini, and Oscar nominee Salma Hayek. The film's casting directors saw Madison and asked her mother if she could act. Her sister took her around a corner and read the lines — and was shocked when the 3-year-old recited them back flawlessly. "My sister was like, 'Oh s***! Yeah, okay. Go in there!'" Madison said, remembering that when she was told her character should be sad, she cried on cue. 

Madison got the part, opening the door to an unexpected career as a child star.

Having appeared in horror, fantasy, comedy, and, of course, Hallmark Channel's "Good Witch," Bailee Madison has demonstrated an impressive degree of versatility as an actor. 

She also displayed that acting was just one of many talents when she teamed up with a friend, writer Stefne Miller, to write a mystery novel, "Losing Brave." Interviewed for InLove, Madison revealed that the book's genesis came when she and Miller were working together on some script adjustments for a movie she was filming. "Stefne turned to me and said, 'Would you ever think about writing a book?' A few minutes later, we had a whole story in our mind and the process began!" she recalled.

The initial concept, however, was far different than what ended up in print, with the two first envisioning a coming-of-age tale with a quirky sensibility. As they dug in, however, they decided that the story they really wanted to tell was a psychological thriller. "So we started toying with that idea," she told Coveteur, insisting that she'd love to tackle another writing project at some point. "I hope so! It's something that I love," she exclaimed.

As previously mentioned, it was her older sister, Kaitlin Vilasuso, who paved the way for Bailee Madison's acting career. Over the years, she's continued to rely on her big sis for guidance and support. "And when I'm doubting myself, my sister is there to remind me who I am and why I do what I do," Madison explained in an interview with Forbes. 

When both siblings were all grown up, they teamed up on their own project; their podcast, titled "Just Between Us," launched in 2018 and ran for 155 episodes until it concluded the following year.

Madison's sister took her surname from her husband, actor Jordi Vilasuso. As fans of daytime dramas should know, Vilasuso's extensive soap opera credits include playing Dr. Griffin Castillo on "All My Children," Dario Hernandez on "Days of Our Lives," and, more recently, Rey Rosales on "The Young and the Restless." Madison has even worked with her brother-in-law, who appeared in her 2017 film "A Cowgirl's Story." Meanwhile, it appears that another generation will be entering the family business, with the Vilasusos' daughter — Everly, Madison's niece — tapped to portray the child version of her aunt's character in "Pretty Little Liars: Summer School."

Back in 2019, Bailee Madison confirmed that she was dating British singer Blake Richardson, one-third of the boy band New Hope Club. Since then, Richardson has become a regular fixture on Madison's social media accounts. 

During a 2024 appearance on "The Drew Barrymore Show," Madison revealed the unusual way that she and her beau came to meet. "I found him online, in the sense that he's in a band, he's a musician," she explained. After she followed him on social media, they began corresponding casually. A year later, Madison was now single when they wound up reconnecting after she'd had a disappointing week on a new dating app. However, circumstances kept them apart — at least in the physical sense. "We didn't see each other for three months," she told the show's host, fellow former child star Drew Barrymore. "We FaceTimed for hours at a time, and then we finally saw each other in person."

Because of their varied schedules — while New Hope Club is on tour, Madison is typically filming a movie or television project — they've gone through extended periods of not seeing each other. However, Madison hasn't found their long-distance relationship to be as problematic as one might imagine. "If it's the right person, you can," she gushed. "I'm proud of our 19-year-old selves for surviving distance and also trying to navigate and grow in your 20s," she told Teen Vogue of their relationship.

For rising star Bailee Madison, one fringe benefit of dating a musician has been the ability to explore her own musical side. In fact, when she and her boyfriend, Blake Richardson, hang out together, they'll sometimes make some music in his home recording studio, just for fun. That was the case when the pair laid down a track while sipping a few glasses of wine. They thought little of their composition until the next day when they listened to what they'd recorded and were blown away by what they heard.

That was the genesis of "Kinda Fun," Madison's debut single, her first-ever pop song. Prior to the single's release in early 2024, Billboard reported that Madison had landed a record deal, signed by Red Van Records (aka the label launched by sibling superstars the Jonas Brothers). While Madison is modest about her musical ambitions, she's hopeful that the song's themes — which she described to People as "holding onto your roots and holding onto your inner child" — will resonate with listeners. "I've been saved by music so many times, and if by any chance I'm able to have that connection with people, that would be such a treat," she added. 

Speaking with The Hollywood Reporter, Madison revealed that her interest in singing goes way back, further than her fans may realize. "It's something I've wanted to do, really, since I was little," she said.

As a Hollywood actor, it would be very easy for Bailee Madison to simply hit her mark, say her lines, and go relax in her trailer until she's needed for the next scene, as so many stars do. Madison, however, sees each day on a set as an opportunity to learn, figuring out how all the various pieces fit together to create a story that will entertain viewers. Over time, she felt an urge to expand her horizons from acting. "And the idea to move behind the lens and care for the entire crew was something that, as a woman in business, was very intriguing to me," she told Forbes.

That was the impetus for Madison to begin producing her own projects. The first of these was the 2016 film "Annabelle Hooper and the Ghosts of Nantucket," in which she also starred. She went on to produce two more films, 2017's "A Cowgirl's Story," and "A Week Away," released in 2020. 

For her first project as producer, Madison put together a team of experienced people with whom she'd worked before, so that they could mentor her through the process. "I really just wanted to get down and dirty with it and I've learned so much," she told Teen Vogue.

As photos of Bailee Madison taken on red carpets will attest, she's got a keen sense of style, and has long been interested in fashion. "Fashion inspires me for so many reasons," she explained in an interview with InLove. "To me, fashion tells a story, it's a way for you to show to those around you and strangers on the street who you are and what you're feeling that day."

That passion for fashion led to an opportunity to create her own clothing when she was approached by retailer Macy's and the This is Nowadays brand, which produces a range of clothing and accessories. As she told Forbes, being able to design her own spring-summer capsule collection — which launched in 2018 – is not something that she took lightly. "To have the chance to design clothes that will hang in someone's closet, that they will wear and create memories in is so exciting," she told InLove.

When sitting down for BUILD Series, Madison marveled at being able to work with a retailer that had long been one of her personal favorite shopping choices. "It's always been a dream of mine to step into the fashion industry, and to be able to do so with a brand like Macy's, which I've shopped at since I was four years old ... it's very full circle," she mused.

In 2022, Bailee Madison was cast in "Pretty Little Liars: Summer School," a spin-off of hit teen series "Pretty Little Liars" that, like the original, is centered upon a deep and ever-unfolding mystery. In the series — which returned with a second season in 2024 — she plays Imogen Adams, a damaged teenager grappling with an unintended pregnancy and a traumatic past. As she explained in an interview with ScreenRant, viewers first encounter Imogen at a particularly dark point in her young life. "Her entire world, everything that was safe to her, everything that was sacred and personal has been taken away," she explanation.

For Madison, Imogen has been a world apart from the kind of roles for which she's best known — the bubbly teenager she played on "Good Witch," for example — and she's admitted that delving deep into the character's psyche was daunting. "This role was the biggest challenge to date for myself as an actor, and also the most fulfilling," she revealed in an interview with The Bare Magazine. "I had to strip everything that I knew, and try my best to completely dive into the mind of Imogen. It forced me to go to some really dark places mentally ..."

Portraying Imogen in "Pretty Little Liars: Summer School," and playing out the character's struggles with her mental health, led Bailee Madison to take a hard look at her own. What she came to learn is that it's ever-changing and constantly evolving, along with the circumstances that arise in her life. "My mental health is a work in progress, as I think all of ours is," she told Wondermind.

That was a lesson that she learned while filming the series' first season and brought with her when she returned for the second. "I was a lot more mindful this season of taking care of my mental health. Last season really put me through the ringer [sic]," she admitted, recalling that after she'd wrapped the first season, her sister observed that she still hadn't let go of Imogen and was only about 20% herself.

Looking back on that first season, Madison recalled having an epiphany that resulted in some serious soul-searching. "I remember having this moment of: I'm doing a show that has always been a dream of mine, and I'm the happiest I've ever been. I'm also the lowest I've ever been," she said. "I didn't necessarily know what to do with that." What she did was begin to build herself back up, to shift her focus to the positive and away from the negative. "From that point on, at my lowest, I was like, okay, we've got to start. And with that came a lot of reflection."

Over the course of her acting career — as a child, teen, and now an adult — Bailee Madison has worked with a who's who of A-list stars, including John Travolta (her co-star in "Lonely Hearts" when she was just three), Jennifer Aniston, Adam Sandler, Bette Midler, Billy Crystal, and many others. One could assume that after working so with many celebrities, she'd be immune to becoming starstruck.

She isn't, something that became crystal clear when she had the chance to meet pop icon Taylor Swift. "The first time I met her, I was filming 'The Wizards of Waverly Place,'" she recalled while answering 17 questions for Seventeen. According to Madison, she was new to the show and feeling a bit nervous when, after a rehearsal, she glanced over and saw the series' star, Selena Gomez, in conversation with Swift. "I just, like, started hyperventilating," Madison admitted. Seeing her freaking out, actor David Henrie walked over and proceeded to introduce her to Gomez and Swift. "I just rambled and started crying," she said.

Years later, she met Swift again during her Red tour. "I did the same exact thing, and that was really embarrassing," she remarked. Each time she's met Swift in the years since then, her reaction has become progressively less humiliating. "We're getting closer now," Madison joked. "She doesn't know it. I know it."

Having worked with some of Hollywood's biggest stars, Bailee Madison has learned not to be intimidated. As she told Forbes, that was wisdom imparted by her mother. "My mom always taught me to look at people as human beings, so when I think about those names I obviously think of their immense talent, but I got to know them on a personal level, and to me that means so much — the conversations I had and will cherish the rest of my life," she said.

Literally growing up on film and television sets, she acknowledged the cast and crew of the TV sitcom "Trophy Wife" — the first time she'd been a series regular — for helping her to develop as an actor. "Oh man, I'll credit the people I worked with because I do think, very early on, I had the privilege — whether I knew it or not — of choosing to be a sponge around the actors I worked with," she explained.

In fact, she told Forbes that each project she undertakes isn't just a job but an opportunity to learn from the more experienced actors with whom she co-stars. "Every person I'm able to work with and become friends with shapes who I am today," she mused.

Of all the lessons that Bailee Madison has taken from all those years spent on soundstages, the biggest has been that creating movies and television is a collaborative effort. "From the moment I started, it became so blatantly aware to me that it takes a village," she told Story & Rain. That knowledge has left her with a desire to expand her role even further; having already stepped in as a producer, she's also eager to direct. "I love a set way too much to just act," she shared. She expanded when talking to Forbes, saying, "Directing is something I'm so ready to do." 

Just as she'd learned from her fellow actors, she's also learned from the directors she's worked with over the years. "I've had the honor to work with incredible directors who've allowed me to shadow them on set," she told Forbes.  

She got the chance to step behind the camera for the first time in 2020 when she directed the music video for New Hope Club's single, "Worse." As she explained in another interview with BUILD Series, the group — led by her boyfriend, Blake Richardson — hadn't been able to make a music video, while Madison hadn't had the chance to direct, which created a win-win scenario for everyone. "I was so happy that I was able to do it with so much support around me and vice versa," she said.