Bailee Madison's Transformation From Child Star To 24

Bailee Madison has had quite a Hollywood career. The fact that she's amassed nearly 60 screen credits is made all the more impressive by the fact that she just turned 24 years old in October 2023. In fact, much of Madison's most memorable work as an actor was captured on celluloid years before puberty beckoned as one of Tinseltown's best respected and most prolific child actors. 

These days, Madison is riding the wave of further success, having successfully made the often-tricky transition from child star to adult roles. She's also managed to avoid the temptations that have sunk so many child actors who came before, emerging as a talented young actor with an established past and a bright future. Of course, spending her childhood on movie and TV sets was admittedly both exciting and strange for the youngster as she learned to navigate the complex world of Hollywood while growing up in front of the camera. "It's been a very surreal experience ... growing up is hard in general and then adding a bunch of strangers watching it happen and commenting freely can be overwhelming at times," she admitted in an interview with Schön! magazine.

With several new projects in the spotlight — including an unexpected foray into music — she's ready to take her career to the next level, and her fans are right there with her. To find out more about this multitalented performer, read on to experience Bailee Madison's transformation from child star to 24.

She booked her first acting gig when she was 2 weeks old

Bailee Madison didn't waste any time getting started in showbiz. Her mother was an actor who eventually booked a TV Office Max commercial for her newborn daughter. As Madison told Variety, she was all of two weeks old at the time. Understandably, she has no memory of that particular job but does recall accompanying her mother and older sister (also an actor) to their auditions when she was just a toddler. Interviewed by Gold Coast's Fort Lauderdale Daily, she remembered unbuckling the restraints in her stroller and "trying to crash their auditions."

That, in fact, was how she got her first big acting role when her sister — 13 years her senior — auditioned for the 2006 film "Lonely Hearts," which boasted a cast including John Travolta, Jared Leto, and the late "Sopranos" star James Gandolfini. "The casting director kind of looked and thought of me and asked, 'Is that your sister?' And she said, 'Yeah.' And they said, 'We had a role that might be good for her. Do you think she would mind coming in?'"

That was how Madison wound up with her first movie role at an age when most kids are still learning to tie their shoes. "Somehow, by the grace of God, I got to do that film ..." Madison said while appearing on "Live with Kelly and Ryan."

Bailee Madison's big break came with Bridge to Terabithia

Being cast in "Lonely Hearts" opened the door to Hollywood, and Bailee Madison burst right through. Her next screen role, in fact, proved to be her breakthrough, the one that put her on the radar of casting directors and got her the kind of attention she hadn't previously experienced. 

"My big break was 'Bridge to Terabithia,'" she told Variety. Discussing "the roles that changed her life" with IMDb, Madison underlined how important that film was to the successful career as a child actor she experienced in the years that followed. "I was five years old when I filmed that movie, and I don't even know how I got to be a part of it, but I did," she said. "Like, my mom and I thought I would just go back to school and be in Florida, like, no one thought anything after that."

From that moment on, Madison's life was never the same. She was cast in guest spots in hit TV shows (including "House," "Unfabulous," and "CSI: NY") and appeared in films, such as "Phoebe in Wonderland," "Letters to God," and "Brothers," playing the daughter of Natalie Portman's character in the latter. Madison's co-star, in fact, became one of her biggest fans. "Bailee is a true actress," Portman told Variety of her onscreen daughter.

She landed her first starring role in Don't Be Afraid of the Dark

In 2010, Bailee Madison was cast in her biggest role to date, starring opposite Guy Pearce and Katie Holmes in "Don't Be Afraid of the Dark," a dark horror fantasy co-written and produced by Guillermo del Toro. Madison starred as Sally, a 10-year-old girl who moves into a haunted house with her dad (Pearce) and his new girlfriend (Holmes) and is the film's central protagonist. "The movie depends so much on the little girl, played by Bailee Madison with pluck, intelligence and a righteous temper," wrote famed film critic Roger Ebert in his review, singling out her performance.

While the film itself is indeed atmospheric and spooky, Holmes ensured that Madison's experience making the movie was anything but. "We'd have dance parties and cupcakes and finger painting," Madison, then 11, told TV Guide of her co-star. "She made such a scary film so much fun."

From there, Madison appeared in various other films, including a memorable turn in "Just Go with It," playing one of the kids of Jennifer Aniston's character in the Adam Sandler-starring comedy.

She's been a longtime supporter of a kids' cancer charity

In the midst of Bailee Madison's hectic schedule as a child actor, she became involved with a unique charity devoted to raising money to find a cure for pediatric cancer: Alex's Lemonade Stand Foundation. The organization is named for Alexandra Scott, who was diagnosed with cancer before celebrating her first birthday, and at age four set up a lemonade stand in order to give the money she raised to doctors working on a cure.

Madison became a celebrity spokesperson for the charity in 2010 and has remained active in the organization's efforts ever since. That's included appearing in public service announcements, as well as other endeavors. In 2015, for example, she launched a lemonade stand in Philadelphia and kept her millions of Instagram followers apprised of her progress. The following year, she issued a personal message encouraging her fans to set up their own stands, reminding children that they can be involved as well. "Remember, you're never too young to make a difference!" she wrote.

Network TV stardom with Trophy Wife

As Bailee Madison's career continued to blossom, she landed some high-profile recurring roles in popular TV series. These included playing young Snow White in "Once Upon a Time," and a female version of Jake T. Austin's character in Selena Gomez-starring Disney Channel series "The Wizards of Waverly Place." Those performances paved the way for her to be cast in "Trophy Wife," landing her first-ever role in 2014 as a series regular in the ABC sitcom starring Malin Akerman. "It's the first time I'm ever gonna be on a 'show' show, and I just hope that everyone loves it," Madison said of the series during a red-carpet interview for Shine On Media. "It's kind of been a whole new, surreal experience for me," she added, sharing her hope that there would be many seasons to come.

Even though many people did indeed love "Trophy Wife" — evidenced by the fact that Slate had declared the show to be the season's best new comedy — her hopes were dashed when it was canceled after its freshman season. While Madison couldn't have been happy about the news, the show's cancellation ultimately freed her up for what would be her longest-lasting TV role to date.

Hitting it big with Good Witch

While all of Bailee Madison's various film and TV projects contributed to raising her profile, it's arguable that none have been as memorable as "Good Witch," the beloved Hallmark Channel series that ran from 2015 until 2021. "I have the honor of playing Grace in 'Good Witch,'" Madison said in a promotional video for the show, discussing her character's supernatural gift. "There's something really, really exciting about playing a character with so many layers," she added. For the teenage actor, Grace's development as a character mirrored what she was experiencing in real life. "The journey of Grace has almost been the journey of me as well and it's been fun to get to relate my character to myself," Madison told the PC Principle.

Madison didn't stick around for the series' entire run, choosing to leave in 2019, after five seasons in the role. "Bailee Madison will always be a beloved member of the Hallmark family," Hallmark exec Michelle Vicary said a statement to TVLine

When the series ended in 2021, Madison paid tribute to all the people she'd worked with on the show, both in front of the camera and behind it. "The cast and crew became family, and what viewers don't get to see when they watch something is every single person behind the camera who make the magic and love possible," she tweeted.

She co-wrote a mystery novel

After leaving "Good Witch," Bailee Madison continued to appear in various films and TV series but also decided to try her hand at something altogether new. The result was her first novel, "Losing Brave," which she co-authored with Stefne Miller. "The book is a psychological thriller that teens can read and the families don't have to worry about the content in the book and the teens can have a safe space to read it," Madison said when describing "Losing Brave" to the PC Principle.

For Madison, the process of writing a novel proved to be illuminating in that the finished product was significantly different than the initial concept. "The book started off completely different than what it ended up," Madison explained while interviewed for BUILD Series. "At first, we had this kind of offbeat, witty, coming-of-age, quirky novel, and then the conversation became ... what have I not done that I would like to do one day? And it was, like, psychological thriller," she added, referencing such literary hits as "Girl on the Train" and "Gone Girl."

Ultimately, the story they settled on was one that delved into a mystery while also spreading a message of female empowerment. "It's a story about self journey, being brave, figuring out who you are, while also figuring out one of the greatest mysteries and fears of your life," Madison explained in an interview with Blink YA Books.

A return to horror with The Strangers: Prey at Night

The same year that "Losing Brave" hit bookstores, Bailee Madison returned to the horror genre, having made an impact years earlier in "Don't Be Afraid of the Dark." In 2018, she starred in "The Strangers: Prey at Night," a terrifying slasher flick — a sequel to 2008's "The Strangers" — about a family being stalked by a trio of homicidal psychos who disguise their identities with masks. This time, Madison starred alongside "Mad Men" alum Christina Hendricks, Martin Henderson ("Grey's Anatomy"), and Lewis Pullman, son of actor Bill Pullman. 

For Madison, it wasn't difficult to place herself in the psychological mindset of a young woman desperately trying to escape a group of murderous maniacs. "It became frightening," she explained to FilmIsNow. "We felt as if we were really living in the elements that we were scared of, which helps ... I was underneath trailers with actual spiders on my leg, and actual dirt on my body, there was nothing superficial or movie-like about it." 

Despite middling reviews, the film was a hit at the box office, bringing in more than $32 million, far exceeding its $5-million budget.

She hosted a short-lived podcast with her sister

As previously mentioned, Bailee Madison has an older sister, Kaitlin Vilasuso, who's also an actor and is 13 years older than her. Prior to marrying fellow actor Jordi Vilasuso, she went by Kaitlin Riley, and has appeared in such films as Oscar-nominated drama "Monster," and "American Idol"-inspired cinematic train wreck "From Justin to Kelly," starring Season 1 winner Kelly Clarkson and runner-up Justin Guarini.

In 2018, the siblings teamed up to launch their own podcast, "Just Between Us." "They open up their lives by sharing personal stories and lessons learned and also bring on loved ones, thought leaders and some of their most treasured friends in the entertainment industry," is how the podcast was described by Podcast One, which produced it. Judging by the episodes produced, they initially had some trouble attracting guests, given that the first few episodes featured their respective significant others, Vilasuso's children. Eventually, though, they welcomed the likes of Chad Michael Murray, Peyton List, Shay Mitchell, and spouses Meghan Trainor and Daryl Sabara.

The sisters packed it in after one year and 55 episodes, with Madison making the announcement on Instagram. "Yesterday we released our final @justbtweenus episode," she wrote. "Thank you so much for welcoming our little show into your lives, sharing moments and stories with us, and for listening to us every week," she added.

She's in a long-term relationship with singer Blake Richardson

Bailee Madison's 3.3 million Instagram followers will occasionally see her post her longtime boyfriend, Blake Richardson, aka one-third of the British pop trio New Hope Club. Reportedly dating since 2019, Richardson has apparently turned Madison into a fan of U.K. soccer club Manchester United, with the two attending games in January 2023 and again that July.

Back in 2021, in fact, she posted a photo in which she referred to him as "my person," and in 2022 celebrated their three-year anniversary by writing, "It's getting better, all of the time. 3 years with my best friend, and my favorite hand to hold. Walking through life with you is priceless."

Madison opened up about her beau during a 2024 appearance on "The Drew Barrymore Show." As she explained, she first became aware of her future boyfriend through his music when she began following New Hope Club on social media. They wound up communicating sporadically online for about a year until they wound up reconnecting via a dating app. "I hearted him, and he, like, hearted me back in 10 seconds," Madison recalled, revealing they got to know each other online for months before finally meeting in person due to their respective schedules. "We've been trying to navigate our 20s together, which I'm so proud of," she added.

She joined a hot franchise with Pretty Little Liars: Original Sin

Bailee Madison joined "Pretty Little Liars," one of television's hottest franchises, in 2021 when she was cast in the spinoff series "Pretty Little Liars: Original Sin." In the reboot of the beloved teen mystery, Madison played Imogen, a 15-year-old with a traumatic past and an unexpected pregnancy. "Imogen's journey in Season 1 has been a true joy for me to play," she said in an on-camera interview for HBO Max.

Speaking with Collider, Madison revealed that the lessons she learned while shooting "Don't Be Afraid of the Dark" all those years earlier continued to resonate with her while filming the suspense-filled TV drama. "So much of what I learned from Guillermo [del Toro] I continue to take with me to this day, especially within ['Pretty Little Liars: Original Sin']," she said. "There were a lot of conversations that I remembered him and I having when it came to 'Don't Be Afraid of the Dark' and little techniques and tactics to kind of get your mind there and your breath pattern there for certain scenes. I carry Guillermo with me in so much of what I do."

She reprised the role when the series returned for a second season in 2024.

She reinvented herself as a singer and landed a record deal

Not only was Bailee Madison celebrating a second hit season of "Pretty Little Liars: Summer School," but 2024 also saw her embarking on a whole new challenge by venturing into the realm of music. To be fair, Madison's interest in music shouldn't be that surprising, given her long relationship with New Hope Club's Blake Richardson. 

In January 2024, Billboard reported that Madison had been signed to the Jonas Brothers' Red Van Records label. The label released her debut single, "Kinda Fun," which she co-wrote with Richardson. The song's genesis, Madison told People, came from drinking a few glasses of wine while she and her boyfriend messed around in his home recording studio. "We went to sleep and woke up and we were like, 'Let's see if we still like it, or maybe I just had one too many glasses of white wine,'" Madison said. "Then I listened to it and we were like, 'It just felt really honest and it felt truthful.'"

Making music with Richardson opened a whole new career path for her and contributed to bringing the couple even closer than they already were. "Now it's so fun because we're writing together," she gushed while being interviewed by Teen Vogue. "We get to just wake up and have coffee and sit outside and then go into the studio and write songs, and it's really special ... a bonding experience."