Brenda Song's Stunning Transformation Since The Suite Life

From 2005 to 2011, Brenda Song was living the millennial dream as a Disney Channel darling, starring as the ditzy but lovable London Tipton on "The Suite Life of Zack & Cody" and its spin-off "The Suite Life on Deck." "I had such a beautiful time on 'Suite Life.' I mean, it was hard, and, like, as with everything, there are ups and downs, but that show is so special," she told Buzzfeed two decades after the series first aired. "I obviously wouldn't be here without that show or without London Tipton, so I look back with nothing but happy nostalgia and smiles," she added.

The star was just 15 when she was cast on the original series, and a lot has changed since her Disney days, which also included the lead role in "Wendy Wu: Homecoming Warrior." But life in the spotlight as a teen wasn't always easy. "It was very jarring for me and started a lot of anxiety because I was trying to figure out who I was at 16. My body and hormones were changing," Song wrote for Glamour. "Suddenly you feel like you always have to look great when you leave the house because what if someone takes a picture?"

Fortunately, Song took the time to figure out who she was and has made big strides in her personal and professional life since then. The beauty went on to become a wife and mom, with big time roles in the likes of "Dollface" and "The Last Showgirl." And her post-Disney transformation is nothing short of stunning.

After saying goodbye to the Disney Channel, Brenda Song landed roles in several TV shows. The talented actor had recurring gigs in the drama "Scandal" and popped up as Daisy in "New Girl" alongside Zooey Deschanel.

She then scored a bigger role in the comedy "Dads," but courted controversy over Asian-American stereotypes on the show. "Coming from the Disney Channel, anything I do is going to offend somehow, somewhere, somehow," Song told Entertainment Weekly. "I love being on a show where the envelope is always pushed ... If you can't laugh at yourself, you can't laugh at all," she added. "I get to do what I've been dreaming about since I was 7 years old. I can't complain."

The star's new life phase was also represented in her style, as the beauty aged up her look in a more sophisticated way than we saw during her London Tipton days. At Elyse Walker's Pink Party, she wowed in a plunging, hot pink top with a high-waisted mini skirt and black, pointed toe pumps. She also attended the Television Critics Association's Summer Press Tour in a classic red midi dress with nude pumps, proving she was ready for a more grown-up chapter as she moved on from her former role.

In 2017, Brenda Song began working on "Changeland," a movie that would change her life. Song starred alongside "Home Alone" actor Macaulay Culkin, and the two fell in love. "Everything's wonderful and I'm happy," she told Us Weekly of their relationship in 2018. Culkin was a little more forthcoming about their romance, saying "I'm probably going to put some babies in her in a little bit," on "The Joe Rogan Experience."

But, career-wise, Song still wasn't where she hoped to be. She told Teen Vogue she hoped to audition for "Crazy Rich Asians," but wasn't given the opportunity. "They said that my image was basically not Asian enough, in not so many words. It broke my heart," she claimed. "I said, 'This character is in her late to mid-20s, an Asian American, and I can't even audition for it? ... I was like, 'Where do I fit?'" 

Song went traveling after the disappointment and gave herself a pep talk to keep pushing forward in her career. Shortly afterwards, Song landed a lead role the movie "Secret Obsession" and TV show "Dollface," alongside Kat Dennings, who's had her own stunning transformation. The beauty still looked years younger than her age, and mirrored that with her wardrobe. She wore ripped jeans, which were a big trend at the time, a graphic tee, and a leather-look jacket to celebrity night at Knott's Berry Farm, as well as a cute pink tee during another visit.

In 2021, Brenda Song became a mom when she welcomed her first child with Macaulay Culkin, a son named Dakota. Song told Glamour she struggled balancing motherhood and work when she returned to "Dollface" three months after giving birth. "I questioned, 'Oh my God, I'm away from my son so much.' After I finished this last season, I needed to take some time off," she said.

The new mom also seemed more interested in expressing herself through style. Though she kept her maternity looks under wraps, her fashion flair was very much alive. She wowed at Gucci Love Parade in 2021 in a belted blue skirt, floral sweater, and coral, pointed toe heels. Song also rocked some bold styles in 2022, including a leopard print jacket and gold-rimmed glasses during a trip to San Diego Zoo. 

Song debuted a new hair look amid the poignant time in her life, too. She showed off her long, dark, locks with bangs in an Instagram photo, revealing the fresh 'do made her feel more like herself again. "She's baaaaaack! ... Thank you for bring[ing] this tired mama back to life! I'm obsessed!" Song wrote. That same year, she and Culkin got engaged.

Around March 2023, Brenda Song and Macaulay Culkin welcomed their second son, Carson. The former Disney actor told The Hollywood Reporter she considered retiring after her family expanded. "I felt like the universe was constantly telling me to just go be a mom,'" she said. But, fortunately for us, Macaulay Culkin knew Song had something special and encouraged her to keep pursuing her career. She got a new management team and booked a role in the 2024 Pamela Anderson-led "The Last Showgirl."

The big change in her life was reflected in how she presented herself, as the beauty felt confident going without makeup in the raw drama. "When you didn't see us in our showgirl makeup, we weren't wearing any makeup. None at all. The first day we tried makeup on and [director Gia Coppola] was like, 'It doesn't feel real,'" she told Bustle. "Pamela being Pamela, she goes, 'I'm not doing it. You guys shouldn't do it either,'" referring to makeup-free beauty Anderson's penchant for ditching cosmetics. And like Anderson, Brenda Song looks fantastic going makeup free.

We also saw the star embrace more sophisticated, darker fashion. She walked the 2023 GFS Fall Benefit red carpet in a long, black-and-white tweed coat over an oversized white shirt dress and tall black boots. She sported a similar palette during Culkin's Hollywood Walk Of Fame ceremony, wowing in an elegant and refined black coat over a ruffled, white collared button down with black pants and stiletto boots.

In 2024, Brenda Song landed a role alongside Kate Hudson in the comedy drama "Running Point," and was very much back in the spotlight. With a renaissance in her career, Song's interest in fashion and designer brands was reawakened, too. She posted a stunning Instagram photo wearing trendy, loose jeans and a white lace top with a black bow. "A moment for this vintage @maisonvalentino from last night," she captioned the photo. 

Song also had us totally floored when she walked the red carpet for the Academy Museum of Motion Pictures Gala in one of her most elegant looks ever. Song's metallic gown – one of the massive fashion trends in summer 2024 – featured a long train from the top of her shoulder, and her stunning plum lipstick proved she'd transformed from a sparkly teen to an elegant woman. Off the red carpet, though, the working mom of two learned the importance of practical fashion. "I love oversized classics with a twist. And now that I'm a little bit older, it's just about being comfortable because I'm running around," she told Bustle.

In 2025, Song's career and personal life was at all-time high. "I think that at 36 years old, you guys are only just now meeting the adult me," she told The Hollywood Reporter. Song added to Marie Claire, "This is the person I've worked really hard to be these last few years. This is the culmination of a lot of self-growth and change in my life." We can't wait to see the next phase of this stunner's transformation.