The Stunning Transformation Of Bailee Madison

Bailee Madison has been a fixture of cinema and TV since, quite literally, before she could stand. The super-talented multi-hyphenate, who's enjoyed massive success as an actor, writer, producer, activist, and plenty more, has grown up in front of our eyes from a sweet little girl into a fierce and powerful young woman. 

It's likely we haven't even seen the best of her yet, given Madison notched up over a decade in the industry, with a whole slew of credits to her name, before breaching her twenties. Still, her transformation from cherubic, apple-cheeked little sweetheart (in 2007's kids' book adaptation "Bridge to Terabithia") into a grungy teenager battling a family of psychopaths (in 2018's gory slasher "The Strangers: Prey At Night") cannot be understated. 

This young lady has some serious range both on and off screen. This is the stunning transformation of the one and only Bailee Madison. 

Madison caught the acting bug young — like, super young, before she could even walk on her own. She followed in the footsteps of her mother and sister, both of whom work in the industry, originally accompanying them on auditions when she was still just a baby. As Madison explained to Miami Living magazine, she would forcibly insert herself into certain situations, admitting, "My mom said I used to unbuckle myself from my stroller and try and crash their auditions."

The wannabe actor, who started off in commercials while still in her stroller, always loved the arts, particularly Broadway shows. She booked her first movie, 2006's "Lonely Hearts," at age 5, off the back of her sister's audition (thankfully, she and her sister were after different roles). As Madison revealed to Miami Living, "I was in the waiting room with my mom. They said, 'Would your sister like to audition? We have this role.' My sister took me around the corner and read with me. I went in and, from that moment on, the journey kinda started."

Although her first movie found Madison starring alongside the big-name likes of Laura Dern, John Travolta, and Salma Hayek, Madison's big break was undoubtedly her star-making turn in "Bridge to Terabithia" a year later in 2007. In 2017, MTV reunited the young actor with her co-star from the movie, AnnaSophia Robb, to reminisce about everything the duo got up to on set 10 years previous. 

They revealed how close the cast was, in particular Madison and her onscreen brother, played by Josh Hutcherson, who was so concerned about hurting her during their many onscreen arguments that he checked she was okay after each take. The little girl caught feelings and even penned a love note to Hutcherson, which he graciously accepted. "He was so sweet, he just hugged me. He took such good care of me. I love him with all my heart," Madison recalled. 

As a wrap gift, Robb and Hutcherson gave their young co-star a very special present, with Madison revealing, "They cut little pieces of fabric from all the clothes my character wore, and they made this fairy costume for me." 

Whether it was alongside screen stalwarts Travolta and Dern or young upstarts Robb and Hutcherson, it took no time at all for the young Madison to get comfortable in front of the camera. By 2009, at just 10 years old, Madison already had a whopping 13 acting credits to her name. Starring opposite Tobey Maguire, Natalie Portman, and Jake Gyllenhaal in blockbuster family drama "Brothers" was just another day at the office. 

Discussing her pivotal, and hugely emotional scene in the movie, with Miami Living, Madison noted, "I was able to work till midnight and it was maybe 11:56 and they just set up for my close up. I think I was able to do one or two takes. I remember just being like 'Oh gosh, I hope we get it.' It was a really fun scene to do. ...That movie was a real blessing to me after it came out, with what it was able to do for me." 

The year 2010 found Madison switching lanes in a big way, starring in her very first horror movie, Guillermo Del Toro's "Don't Be Afraid of the Dark," alongside Guy Pearce and Katie Holmes. Speaking to AXS, the young actor noted she didn't feel any pressure stepping into this darker world, "But it was definitely very new to me; especially filming a scary film." Madison acknowledged, however, she "learned a lot and it was hard; but, definitely worth the experience."

The most difficult element was working with a variety of computer-generated creatures — none of which, naturally, were actually on set. "They were never there! There was never anything," Madison admitted. "Sometimes there was a piece of tape or sometimes there was just nothing. You just kind of, day by day, gradually got a little bit used to it." The then-10-year-old pledged to watch more horror movies as a result of her experience, noting, "Now that I've done a scary movie I'm okay with scary things. Not like 'A Nightmare on Elm Street' or anything like that, but I like a classical suspense."

Just a couple years later, after an appearance in Adam Sandler vehicle "Just Go With It" really put her on the map, the young actor switched gears yet again with 2012's "Cowgirls 'n Angels," a spirited indie drama about a group of rodeo riders. She told The Hollywood Interview that working with veteran actors such as James Cromwell ("the definition of humble") was everything she'd hoped for and more. Of co-star Alicia Witt, Madison remarked, "She started acting even younger than I did, and has made the transition into an adult actor so seamlessly, plus she's a really talented musician and has so many diverse interests. She was a great role model."

In a chat with Behind the Lens Online, Madison claimed her time on "Cowgirls 'n Angels" was incredibly rewarding, too. "Really, for me, there's no scripts out there like this one. It was full of love. It was full of heart and it was about faith and hope and courage. For me to be a part of it... was such an honor. I just love the script. I just love everything about it," she gushed. 

As Madison entered those all-important early teen years, her résumé continued to grow. She joined hit show "The Fosters" in 2014, sticking around for two seasons before departing in 2016. The young actor was, by that stage, becoming a small screen staple, having appeared in the likes of "Wizards of Waverly Place," "Trophy Wife," and "R.L. Stine's The Haunting Hour," among others.

The Fosters was an easy choice for Madison, as she detailed to Your Teen Mag. Choosing roles is a "family affair," as, "My sister reads the script first, then it goes to my mom, and if they both like it, then I read it. A lot of scripts are quick to take you from a 15-year-old to a 17-year-old overnight. So, we say 'no' more than we say 'yes.' We're selective and we try to keep things age appropriate. We approach every script that way and always have."  

In 2015, Madison was the victim of online trolls as she was labeled a prude. Rather than ignoring it, the actor took to Tumblr to pen an inspirational essay. With that, a space for her to turn when things get rough, to preach kindness, and to share her innermost thoughts and feelings was born. And, alongside it, the #IamMoreThanAWord social media movement. 

Madison told By You magazine she's all about kindness and empathy, opining, "We are all here to have a voice and make a difference; we all have a choice. It's as simple as walking down the street — you can ignore a person or you can smile, say hello, or even something nice. ...It may not seem like a big deal, but it's a choice in life that you can walk past things or help that person feel better. It's a constant choice every day to help even one person with that light or that smile — and if you don't, you're missing something. I think it's our job to help give a little push and help spread the lightness." 

Madison started seeing fellow entertainer and social media star Alex Lange in 2016. On a Dec 2018 episode of her podcast "Just Between Us," which Madison hosted alongside big sis Katilin Vilasuso, she opened up about what made their coupling so strong.

As reported by E! News, Madison revealed Lange had expressed his undying devotion the very first night they met. The actor waited a full six months before saying "I love you" back, however her beau acknowledged it was worth the wait. The duo initially spent three months apart at the beginning of their relationship, talking on the phone constantly in the interim. 

Lange subsequently sent her a photo of a pebble. She explained, "He goes, 'Do you know what penguins do when they choose their mate for life?' And I go 'No,' and he goes, 'They give them a pebble. So here's a pebble.'" Sadly, the romantic gesture wasn't enough to sustain their relationship for the long haul – ET reported in January 2019 that the couple split.

In keeping with her impressive growth and maturity, in 2016 Madison stepped behind the camera to produce a couple movies of her own, namely kids' adventure "Annabelle Hooper and the Ghosts of Nantucket" and "A Cowgirl's Story," released the following year. She also had starring roles in both.

The actor-turned-producer gushed to The PC Principle about the process. "It was one of the most gratifying experiences because as a producer, you are working for the sake of not just yourself, but for the rest of the crew. So, Kraft services, grips, the lighting department, animal trainers and the cast are all following your hands to try and make the set to be as smooth and enjoyable as possible," she enthused.

Madison went on to explain how grateful she was for the opportunity, acknowledging, "For me to be trusted with fellow producers and a wonderful director who has been doing this for such a long time, it was a very humbling and wonderful experience." 

In January 2018, Madison proved how multi-talented she is by publishing her first book, "Losing Brave." Co-written with author Stefne Miller, the YA thriller highlighted a moment when Madison was anything but cowardly. Speaking to Teen Vogue, the then-18-year-old noted, "We decided to go in the more psychological aspect because that genre is really picking up right now in the world of books and movies, but it doesn't really exist right now for teenagers."

Madison was apprehensive about putting herself out there, admitting, "It's a really exciting and nerve-wracking new chapter in my life and I love the book world so much. I think it's such an amazing kind of relationship that can be formed between the person who's reading and you just kind of sitting and imagining what this world is in your head."

She told CBS Local that the main character, Payton, was inspired by both authors' experiences. "I think Payton specifically was inspired by parts of myself but also stories that Stefne has actually gone through at my age and memories she has so, um, it was both of us collaborating," Madison said. 

That very same year, Madison returned to her horror roots with "The Strangers: Prey At Night," as a grungy and badly behaved teenager fleeing for her life from mask-wearing psychopaths. She told Dread Central the movie came around at just the right time, as "I had actually been reading so much at that moment in my life. I just had yet to find a horror script that was so smart and so different and engaging, yet grounded." 

Madison was attracted to the physicality of the role, noting, "It's very detailed in the script and very stunt oriented and very physical. ...I truly never played a character like her before. I wanted to know more about her." Likewise, Madison gushed to Daily Dead, "I'd done some physical stuff before, but that usually happens at the end of filming. In this, every single day I wanted to have bruises on me, I wanted to feel drained because that meant I was putting in the work. Thankfully, the stunt team was all in. ...They let me do everything except for one shot. ...I really got put through the wringer for this, and I'm so glad I did."  

Madison stretched herself even further with a clothing line for Macy's in-house imprint, Nowadays. She told Darling magazine in 2018 that, although there's a lot on her plate, their collaboration was meant to be. "It feels organic only because I don't like being comfortable; if I feel like I've done it before, I start to freak out. I've always wanted to do a fashion line — always. And I've been approached by multiple people throughout the years and I've said no. ...I have shopped at Macy's since I was a little girl — so, when a store that I loved and I think is a really great place for families came to me, well, that was a no-brainer," she explained.

Madison went on to advise that writing Losing Brave came about in a similar way — because she felt a bit stagnant elsewhere in her career, and wanted to fill a gap — while producing was a must simply because she loves being behind the camera. "I think the go, go, go factor is something that can play into it, but I love what I do and I've loved everything that I've done, so it's felt very me," she acknowledged.  

In spite of having fingers in plenty of different pies, acting continues to be Madison's first love. Starring on Hallmark family show "Good Witch" felt like the ideal spot for her as a young actor transitioning into being an adult. In 2019, Catherine Bell, who plays her onscreen mother, gushed about Madison's professionalism to Reel Life with Jane.

"Oh, my God, Bailee is phenomenal. She's just such an amazing... I mean, I've got to say I've worked with some child actors in this business, and she is just unbelievable. She's one of a kind. Sweet, down-to-earth, humble, kind, loving. ...In my scenes with her, I often feel like I'm talking to my daughter. It's just so easy to be emotional," she enthused. 

The feeling is clearly mutual, as the young actor told Assignment X back in 2017 just how much the show meant to her, noting of her character Grace, "What I've always loved about this show is, it's not necessarily power, it's what's within the heart, and I think, as she grows up, her heart strengthens, and her love for others does as well." 

Given how young she started, it makes sense that Madison she felt older than her years — even before she turned 20. In a 2018 interview with Schön magazine, she looked back on a life in front of the cameras, advising, "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. However, I feel incredibly fortunate and blessed with the amount of love and support I've been given, and the memories I've been able to make."

Madison also acknowledged her own positive attitude to life, noting, "I've always been told that ever since I was little I've always just loved life and I think the same goes for me now. I love people, I love spreading love and I love enjoying moments, and as cheesy as that may sound, I love smiling and laughing. I just do." When the darkness hits, she knows how to handle it, explaining, "However, like anyone, I have low moments and that's when I try to take a step back, surround myself with my family, my true core of friends and remind myself how blessed I really am."  

Bailee Richardson's private life came tumbling out into the open when she began sharing social media posts indicating that she had a significant other. That was evident in 2021 when she posted a photo on Instagram of herself and her boyfriend, singer Blake Richardson, whom she'd been dating since 2019. In 2022, she shared a post celebrating their three-year anniversary, referring to Richardson as "my best friend, and my favorite hand to hold."

Richardson, of course, is a member of the British boy band New Hope Club, and it was her admiration for his group that initially brought them together. As she revealed during a 2024 appearance on "The Drew Barrymore Show." it all began when she began following New Hope Club on social media — which led to Richardson reaching out to her directly. For the next year, the two sent messages to each other and then wound up bumping into each other on a dating app. "I hearted him, and he hearted me back in 10 seconds," Madison said. 

That initial flirtation set the stage for the two to grow closer, getting to know each other on a long-distance basis while communicating via FaceTime when they were both 19. It wasn't easy, Madison told Teen Vogue in 2024, shortly after they celebrated their fifth anniversary, but they persevered. "I'm proud of our 19-year-old selves for surviving distance and also trying to navigate and grow in your twenties," she said.

When Bailee Madison signed on to star in the 2021 Netflix musical "A Week Away," she wasn't just an actor for hire — was also one of the project's producers. In the film, Madison portrays a regular attendee of a Christian summer camp who befriends a new arrival (Kevin Quinn), a troubled teenager who's only there on a judge's order (which he chose over the judge's alternative, a juvenile detention facility).

According to Madison, working on the film was one of her professional high points. "It was simply a joy all around," she gushed in an interview with Brief Take. Being able to take a hand at shaping the project as an associate producer, she added, was also a thrilling experience, particularly given her youth. When speaking with Mom the Magnificent, she detailed more of her experience, saying, "I learned so much about my voice and the creative process by being part of the larger collaborative process. I couldn't be more grateful for that opportunity."

Taking the reins by producing her own projects is becoming increasingly common for heavyweight female actors in Hollywood, representative in the stunning transformation of Reese WItherspoon, yet it's highly unusual for someone of Madison's age. As she told Rose & Ivy, however, taking that step in her career was a natural progression in a career that began when she was just a kid. "I do think the life I have lived has given me a sense of confidence," she said.

"Edgy" is not a word that has typically been used to describe Bailee Madison — at least until she was cast in a bold and provocative role in "Pretty Little Liars: Original Sin," a spinoff series of the sinfully salacious teen drama. While there were various rumors and spoilers about "Original Sin," when the series finally debuted in 2021, fans discovered that Madison played Imogen Adams, a pregnant teenager mourning the recent death of her mother while also harboring some awful secrets. As Madison told TVLine, pretending to an expectant mom required wearing a pregnancy prothesis for several months. "I ended up getting actual back pain, which I had to work out after, but it was an experience," she said. "It was definitely a first for me — one I was excited to get to do."

Madison opened up more about her excitement in taking on the role when she was interviewed for HBO Max, the streamer that broadcast the series. "Imogen's journey in Season 1 has been a true joy for me to play. ... There's such a level of strength and passion that drives Imogen, every single day, to keep going," she said.

In addition to being able to bite into such a juicy role, Madison also embraced the experience of being part of an all-female ensemble cast, bonding tightly with her co-stars. "The sisterhood and the womanhood that I've been able to actually feel for once in my life fully ... is a big part of why I would [like to be on] the show for just a lot of years to come," she told Teen Vogue.

Dating a successful singer and songwriter clearly rubbed off on Bailee Madison, which manifested when she began to pursue her own musical aspirations. It was immediately clear that Madison was very serious about her music — so much so that she signed with Jonas Group Entertainment, the management group run by Kevin Jonas Sr., aka father of the Jonas Brothers. "I'm finally ready to take this leap," she told Variety. "Music is a very personal and vulnerable side of me ... sharing this part of myself with the world means so much, and it feels like a chance to give insight on my heart." 

It took a few years, but Madison wound up with a record deal, her musical ambitions finally coming to the forefront in 2024 with the release of her debut single, "Kinda Fun." The song was the result of a collaborative songwriting session with boyfriend Blake Richardson, with the two bolstered by a few glasses of wine. The next morning, she listened to what they'd come up with to see if it held up after the effects of the vino wore off. "Then I listened to it and we were like, 'It just felt really honest and it felt truthful,'" she recalled in an interview with People.

The theme of the song is evident in its title, an ode to the power of ensuring fun is also part of one's life. "It's kind of a hug to my younger self, and then kind of a pat on the back I would give to my current self to bring the fun back into everything again," she explained. In July 2024, Madison followed up "Kinda Fun" with a second single, "Chiller."

While music consumed some of her time, Bailee Madison never strayed far from her main vocation as an actor. That included a multi-episode stint in 2023 series "The Hardy Boys," a guest spot on the TV series "Good Trouble," and a return to the world of "Pretty Little Liars" for a second season in 2024 (which, unfortunately for fans, was also its last).

In 2024, Madison signed on for a project that returned her to the rom-com realm, "40 Dates and 40 Nights." In that film, Madison was set to star as Leah, who — unlike the actor herself — has been decidedly unlucky in love. Her grandmother Gigi ("Young Sheldon" alum Annie Potts) makes her a deal — if Leah can't find love after going on 40 back-to-back dates, then she'll pay her rent for an entire year. 

In May 2025, Madison landed another gig, joining the cast of "Rocky Top College." With a screenplay from Jarnell Stokes (a former NBA star who gravitated toward filmmaking), the quasi-autobiographical story follows basketball prodigy Zion Williams (Jabari Banks), ranked as America's No. 1 hight school player, who shocks everyone by eschewing a major university to enroll in a small, obscure college.