Brenda Song Reintroduces Herself: On Running Point, Child Stardom, and Life With Macaulay Culkin

Brenda Song is sitting in an IHOP when it hits her: She has no idea what she wants. It’s 2011; she’s just ended a long run at Disney Channel, where she’d starred in various original movies and spent six years playing Paris Hilton–inspired hotel heiress London Tipton on The Suite Life of Zack and Cody and its spin-offs. “There was six months where when I got into a car, I would automatically just drive to set,” she recalls during a recent Zoom with Vanity Fair.

Back at IHOP, Song had rattled off her order on autopilot. Then she paused. “I took a second and went, ‘I don’t know if I want an egg white omelet…. That’s what someone’s brought to me for eight years. I don’t know how I want my eggs!” says Song. “I had the craziest weird breakdown over eggs. Because it was the first time after eight years where I was like, ‘What do I want?’” she continues. “I couldn’t quite grasp things.”

Thirteen years later, Song found herself at another crossroads—questioning her future as a working actor after welcoming two children in quick succession with fellow former child star Macaulay Culkin. “I just felt like such a new person, like a blob of clay, and I’d never felt that way,” she says now. “All of a sudden I’m like, Wait—my body doesn’t feel like my own, and my priorities are so different.”

“The world doesn’t know where to put you if you don’t know where to put yourself,” she continues. “I just was feeling insecure, to be honest, and like I didn’t know where I fit in this industry…. I had literally told my mom and my partner, ‘If the best of my career is behind me, I think I’m okay with that.’” Song recounts all this in fast-paced disbelief, seemingly eager to get to the part where she comes to her senses: “It just goes to show you how quickly life can change overnight.”

Just six weeks and a change of management later, two of the most exciting projects of Song’s career landed at her doorstep. Earlier this year, she appeared alongside Pamela Anderson in Gia Coppola’s awards season hopeful The Last Showgirl. She’s now starring opposite Kate Hudson in Running Point, a new series from Mindy Kaling streaming on Netflix. Song had only eight days to dust herself off from the “very spiritual experience” of playing hard-edged showgirl Mary-Anne in the Las Vegas desert before returning to her sitcom stomping grounds in Los Angeles.

In Running Point, Song plays Ali Lee, no-nonsense chief of staff to Hudson’s basketball team president, a character based on series executive producer and Lakers owner Jeanie Buss. It was a dream assignment for the actor, whose dressing room on The Suite Life was home to a life-size Kobe Bryant cutout. Song even wore her Lakers championship ring to her first meeting with series cocreators Kaling, Ike Barinholtz, Elaine Ko, and David Stassen.

“I was honestly nervous when I sat down with them, because I love the Lakers so much,” says Song. “There have been other shows about the Lakers,” she continues—most recently, HBO’s short-lived Winning Time—“and it’s really hard for me as a lifelong fan to watch something where I feel like, ‘Wait, that’s not how that happened.’” But she was assured that Running Point, which centers on the decidedly fictional Los Angeles Waves, is not meant as a straightforward biography. “This is a vehicle to meet this crazy dysfunctional family and workplace family,” Song was told. “And I was like, ‘I’m in.’”

Even so, Song prepared for the part by spending time off-screen with Linda Rambis, the longtime Lakers exec on which her character Ali—named for Rambis’s real-life daughter—is based. “I loved her grit,” says Song. “She’s so confident in her ability to do her job. I feel like I’m constantly questioning myself. Am I getting fired? Am I okay? Ali is so opposite because Linda knows what she’s doing—there’s no hesitance about it.”

The project also became something of a family affair. While visiting his fiancée on set, Culkin filmed a spontaneous cameo as a disgruntled Waves fan who appears during the season’s penultimate episode. Song breaks into a smile whenever Culkin is mentioned, and says building a family with him is what made her reevaluate her professional desires. “Finding a lot of fulfillment in my personal life brings me a lot of confidence,” says Song. “I know that, for better or for worse, regardless of what job I get, having a partner who just loves you unconditionally and supports you fuels you into being able to take risks.”

While acknowledging that “the most important role I’ll ever play in my life is mom,” Song also admits that being her best self for her kids sometimes means being away from them on a set: “I don’t know who I’d be without my work and my job.” Accepting that contradiction is a work in progress. “I’m figuring it out as I’m talking to you,” Song says with a laugh and a shrug.

If The Last Showgirl is about a chapter in one woman’s career ending and Running Point is about another woman’s beginning, Song finds herself somewhere in between. “Being reintroduced to the world at 36 feels crazy after being in this industry for so long,” she says. “For the first time, I feel like I’m in control of my life and my career, and I feel so fulfilled in both aspects of it.”

Song started acting at the tender age of six. “Growing up in this industry is very tricky because not only are you trying to find your way as a human being, learning, making mistakes, but everything is amplified because of your profession,” she says.

She found early success as a performer on Disney Channel during its mid-2000s heyday, booking supporting roles in the 2000 Disney Channel original movie The Ultimate Christmas Present, 2002’s Get a Clue alongside Lindsay Lohan, 2004’s Stuck in the Suburbs, and a recurring role on the original series, Phil of the Future. But it was 2005’s The Suite Life of Zack and Cody, a comedy of errors about twin boys (Cole and Dylan Sprouse) living in a luxury hotel, that changed Song’s life before it even aired. Around the time she was cast to play an obliviously spoiled heiress, Song also got accepted into Harvard.

“I always hate telling people that story, because that feels like such a flex,” Song says. “But it’s also something I’m really, really proud of, because I worked really hard. I have no regrets whatsoever…. It was never really even a choice. I couldn’t imagine myself as a full-time student. I would’ve gone crazy. I would’ve driven everyone crazy.”

Perhaps it was Song’s proven potential outside of the Disneysphere—or her lack of pop star aspirations—that kept her from being defined in the same way as contemporaries like Miley Cyrus, Selena Gomez, and Demi Lovato. “My parents really kept this as an after-school activity. I was such a homebody,” says Song. “I wasn’t going out with all the crazy kids.”

While shooting 20-plus-episode seasons of The Suite Life of Zack and Cody or its nautically themed spinoff, The Suite Life on Deck, Song soaked in everything she could about show business. “I was really fortunate to have incredible creators on Suite Life who understood my curiosity for this industry—allowed me to sit in the writers room, to see all aspects of how this show was run. I had a bullpen in the production office,” says Song. “I walked away with this deep appreciation for our industry.”

But as she neared the end of her 150-episode run with Suite Life, “I was just creatively ready to move on,” says Song. She was reportedly prevented from advancing in the audition process for Clint Eastwood’s Gran Torino because the film implies that the character she would have played has been raped. But when a second auteur offered her a gig, Song refused to bow out. And this one gave her a chance to go to Harvard, too.

“I was very lucky that my first proper job at the end of [Disney] was The Social Network,” says Song, who played Andrew Garfield’s appletini-sipping, fire-starting collegiate love interest Christy. “We had rehearsal time, and so I had time to work with David [Fincher]. I remember sitting down with Andrew and Jesse [Eisenberg], and we’re reading the script, talking through it, and I was like, Oh God, I missed this,” says Song. “I had to come back down to my gut, my core.”

She graduated from Fincher and Aaron Sorkin’s fictional Harvard and entered the entry-level work of playing assistants on Shonda Rhimes’s Scandal and the Fox sitcom Dads, as well as searching 20-somethings on New Girl and Hulu’s Dollface. It was exactly the trajectory Song needed. “Being a child actor, it’s interesting, because you learn to emulate a lot of feelings,” she says. “This is what sadness looks like. This is what it sounds like. But until you feel it, you can’t truly, on a really grounded level, get there.”

More than a decade of perspective on her “crazy overacting” at Disney has allowed Song to fully embrace her time on the network. “It’s really interesting now to see those shows come back around. More than ever, I’ve had people come up and talk to me about Wendy Wu: Homecoming Warrior,” the 2006 Disney Channel original movie that gave Song long overdue top billing for the first time. “Disney was honestly very ahead of the curve when it came to colorblind casting,” she says, “being able to give opportunities to kids of all ages, sizes, colors, ethnic backgrounds, nationalities to tell their own stories.”

Her lovably ditzy hotel scion, who was recently floated as a worthy addition to The White Lotus universe, also has an enduring legacy. “I would love London Tipton to be in White Lotus. Are you kidding me? That would be hilarious,” Song says about the memes. “I always wonder what an adult London Tipton would be like.” So does Song’s six-year-old niece, who recently began watching Suite Life. “The beautiful thing about our art form is that it lives forever,” she says. “If you’re lucky enough to make a show that can be somewhat timeless, it’s so interesting to see what different generations take from it.”

And Song learned to take her experiences away from Disney soundstages into the next phase of her career. “Being able to draw from your own personal life just makes things feel so much more organic. It’s crazy how life experience translates into acting,” Song says with a sarcastic grin. “Savannah, I’m not an actor. I’m a reactor,” she adds, with a hair flip that recalls both her sitcom persona and the woman I’ve been getting to know over Zoom.

Song’s private happiness became the public’s business when she and Culkin brought their two children—Dakota and Carson, now three and two years old respectively—to his Hollywood Walk of Fame ceremony in December 2023. “It was just something that was so special. There was no way that we didn’t all want to be there to enjoy it,” says Song. “But it is nerve-wracking because it’s really personal and sacred. You know how the world is—you put it out there, and it’s like you can never take it back.”

More recently, Song and Culkin made their love story headline news with a Cosmopolitan cover in which they recalled their 2014 meet-cute through mutual friend and fellow former child star Seth Green, who later reconnected the pair for his 2019 film Changeland. “It’s scary, but at the same time, freeing, because we don’t have to pretend or hide. We can just be us,” Song says of bringing their guarded romance out of the shadows. “He’s my biggest supporter, and we do everything together anyway. People are just putting more of a spotlight on it now.”

The world has been parasocially tickled to see that Home Alone’s Kevin McCallister and London Tipton ended up together—a fan fiction fever dream for those in the zillennial microgeneration. “People have been so sweet about it. You have to embrace it,” says Song. “How can you not take that in?”

And if either of their sons want to pursue acting? “I know one of my sons is going to try at some point. I mean, that’s all they know. Both their parents are actors,” says Song. “Regardless of what our kids decide to do, we’re just facilitators of their hopes and dreams and passions. We will encourage it, but I just want them to enjoy being kids and wait until they’re older.” Although she is all too familiar with how stubborn children with a performative streak can be. “I was a very, very passionate kid, and I couldn’t imagine if my mom told me no,” she says. “I have no idea what I would’ve done.”

As for her own career, Song is eager to return for a potential second season of Running Point. From there, “I’m so excited for the unknown. I want to be scared. I want to push myself out of my comfort zone,” she says. “Even if I think I’m out of it, I want to be pushed further.”

“I feel like the best is yet to come,” Song adds. “I want to find my Last Showgirl—a role where I feel like there’s no one else that could play this but me.” And she’s no longer afraid to order exactly what she craves. “I’m able to stand up and speak up for the things that I hope for and truly want,” says Song. “I was too scared to do that for a very long time.”