Busy Philipps' Hollywood Life & A Look At Her Unconventional Relationship With Her Ex

Busy Philipps has been a fixture on television screens since landing her first small-screen part in the late 1990s. "I was so lucky to get that at 19," she told the Independent. "Especially in that moment, I was so vulnerable to the industry. I wanted it so bad. I would cry at night longing for a chance to be on a TV show." Since then, she's racked up more than 70 screen credits. Among the more memorable characters she's played: devoutly religious medical intern Dr. Hope Bobeck on "ER" during the 2006-2007 season; Laurie Keller, freewheeling BFF of Courteney Cox's character on "Cougar Town" for the entirety of the sitcom's six-season run; Gale Liptrapp on HBO comedy "Vice Principals," ex-wife of star/co-creator Danny McBride's character, Neal Gamby; out-of-control heiress Sheba Goodman on "Unbreakable Kimmy Schmidt;" and Summer Dutkowsky, member of newly revived girl group on Tina Fey-produced comedy "Girls5eva." 

And while acting may be her primary vocation — and what ultimately put her on the map — she's become more of an all-around pop-culture celebrity, thanks to other pursuits within the entertainment industry that have allowed her to be herself. That's particularly true on Instagram, where she's built an impressive following. Meanwhile, Philipps has also made headlines for announcing some big news about her marriage, which had taken a somewhat unorthodox turn.

To find out more, read on for a deep dive into Busy Philipps' Hollywood life and a look at her unconventional relationship with her ex.

Premiering on NBC in 1999 and airing for just one season, "Freaks and Geeks" remains a cult favorite beloved by fans. Perhaps even more importantly, however, the Judd Apatow-produced teen comedy also possesses what is arguably one of the most impressive track records for launching future stars. Busy Philipps was among that young cast, which also included Seth Rogen, Linda Cardellini, James Franco, Martin Starr, John Francis Daley, Jason Segel, and Lizzy Caplan. For Philipps, "Freaks and Geeks" paved the way for everything else that was to come. "I think we are all proud of each other for what we've accomplished," Apatow told Variety of the talented young cast he assembled. 

Despite the launching pad the series provided, Philipps' experience on the show was not entirely pleasant — primarily because of co-star Franco, who played the brooding boyfriend of her character. "James Franco and I really didn't get along," Philipps divulged during a 2016 appearance on "Watch What Happens Live," noting they'd "since made amends." According to Philipps, she and Franco "really, really disliked each other" while working together, describing an incident when he pushed her so hard that she fell to the ground. 

"At the time it felt very dramatic," she told Backstage. "Now I think, How cute were we? We were such little a**holes! I really adore him now."

Following the cancellation of "Freaks and Geeks," Busy Philipps' next TV gig as a series regular came when she joined "Dawson's Creek" in its fifth season. Philipps was just 21 when she was cast as aspiring singer Audrey Liddell, college roommate of Katie Holmes' character, Joey.

While filming the show in Wilmington, North Carolina, she and the show's other young stars would regularly get into some hijinks in various Wilmington watering holes. "I just feel really lucky that TMZ and the internet didn't exist," she admitted during an appearance on "The Late Late Show with James Corden." "I would probably not be sitting here if it did — I would have been TMZ'd out of Hollywood."

As "Dawson's Creek" fans will recall, Audrey was last seen preparing to hit the road as a backup singer for John Mayer. Speaking with Dish Nation, Philipps shared her thoughts on where Audrey might be now, 20 years later. "I think she probably moved to Nashville, she tried her hand at some sort of career, singing, and then she married some rich guy and is living back in Beverly Hills, and she has kids, and is just a mom," said Philipps, admitting that she created that intricately detailed scenario right on the spot. She also envisioned a future for Audrey in an entirely different entertainment genre beyond music. "I feel like reality TV definitely called Audrey's name," she quipped.

While she was a member of the "Dawson's Creek" cast during the show's final two seasons, Busy Philipps met co-star Michelle Williams. It would prove to be one of the most important encounters of both their lives, sparking a friendship that has endured for two-plus decades. "It was like, you know, how people say love at first sight? We had that thing. We had that friend connection. It was just an immediate: 'Of course we're drinking wine and smoking cigarettes and getting in bar fights,'" Philipps told Entertainment Weekly of what initially drew them together.

The feeling is certainly mutual, and the bond that formed on "Dawsons' Creek" has only grown stronger over the passing years. "I'm so in love with her," Williams told People of Philipps. "She's proof that the love of your life does not have to be a man!" 

To this day, the two remain closer than ever — so close, in fact, they've become regular fixtures together on red carpets, with each happily agreeing to accompany the other at entertainment industry events, award shows and assorted Hollywood shindigs — in fact, nominee Williams brought Philipps as her date for the infamous 2017 Oscars. "It makes it fun," Williams told Page Six of why she continues to invite Philipps to be her plus-one. "These things can be a little ... I don't know if you ever really get used to being on a red carpet."

In 2018, Busy Philipps made a bold career move when she launched her own late-night talk show, "Busy Tonight," premiering that October on the E! channel. Days before the debut, it was reported that the show had scored a major coup, with Tina Fey joining as executive producer. Sadly, E! canceled the show just a few months later. "They decided not to pick it up," Philipps told her followers in an Instagram Story, reported by Vanity Fair. On New Year's Eve of 2019, she revealed she'd been "blindsided" by the cancellation in an Instagram post that included a handwritten note to E! from her daughter Birdie, reading, "You are the worst TV network EVER ... You suck."

Just over a year later, Philipps rebounded by launching her own podcast, "Busy Philipps is Doing Her Best." Ironically, the cancellation of "Busy Tonight" inspired the podcast, in which she and celebrity guests discuss how obstacles they encountered wound up opening doors to something even better. "It started during the pandemic with the idea that [co-host] Caissie [St. Onge] and I would tell each other and our listeners what we were doing our best at that week, to give ourselves a little credit for how we've been moving through the world," she told The Daily Front Row. The notion that massive disappointments can reveal new paths to success, she'd come to discover, was universal. "Everybody has those stories," she added.

In May 2022, Busy Philipps made a surprising announcement on her podcast, "Busy Philipps is Doing Her Best." She and husband Marc Silverstein had separated — more than a year earlier. "Marc and I talked about it, and when we first separated, we couldn't even think about putting one of those statements out — it made us sick, both of us, truly ill," Philipps said, explaining why she'd waited so long to share the news. 

As for how they were handling their shared parental responsibilities, Philipps explained they'd agreed to try "nesting," in which their kids live in the family home, with each parent taking turns living there with them. In their case, due to COVID-19 and other factors, there were occasions when their rotations in the home would overlap, at times resulting in she and Silverstein cohabitating. "Obviously, it's not for everyone," Philipps admitted. "There's a lot of complication and hardship within the arrangement sometimes for the two of us." 

Of course, anyone who was paying attention couldn't have been that surprised, as Philipps has spoken candidly about her marital difficulties over the years. "Marriage is always hard, but especially when you have kids ... You're going to go through periods when you're not into it, but there always has to be one person willing to fight," she told Parents in 2018. "I went to Marc several times and said, 'I cannot do this anymore. Something has to change, and it's you.'"

During her marriage to Marc Silverstein, Busy Philipps gave birth to two children, both daughters: Birdie Leigh, born in 2008, and Cricket, whom she welcomed in 2013. She delivered her first child, she told Us Weekly, without any pharmaceutical assistance. "I had a baby with no pain medicine, mainly because most people I talked to didn't think I'd be able to do it," she declared. "So there." That defiant I'll-show-you aspect of her personality, she admitted, was also likely responsible for her choice of vocation. "That's also kind of the reason I'm an actress," she quipped.

Not only did Philipps choose to not avail herself of an epidural during Birdie's birth, she also prepared for the arrival by taking Hypnobirthing classes. Hypnobirthing, for the uninitiated, involves learning various self-hypnosis, breathing and relaxation exercises in order to minimize anxiety leading up to the delivery date, and has been adopted by celebrity moms such as Beyoncé, Angelina Jolie, and Kristen Bell. 

While Philipps has given numerous interviews declaring her love of motherhood, there's one aspect of the pregnancy experience she could have done without. "I'm able to intellectually appreciate the fact that my body has done a truly incredible thing, but I don't love the extra skin," she told Parents magazine. "People say, 'Wear it like a badge!' Um, yeah, that doesn't speak to me. I'd rather have a flat stomach."

When it comes to raising her daughters, Busy Philipps prefers playing it by ear over elaborate planning. "I call myself the all-over-the-place, doesn't-have-a-plan mom. Is that a parenting philosophy?" she told Parents. That same attitude also holds true with her approach to disciplining her kids, something she admitted hadn't been working out particularly well at that particular moment. "We're flailing in the dark when it comes to discipline. Nothing works!" she complained, noting that whenever she threatened youngest daughter Birdie with consequences it would get her nowhere. "So, we don't really do punishments," she explained. 

One controversial child-rearing technique she's eschewed is the concept of the "family bed," in which children and parents sleep together. "We're not co-sleeping," she revealed in an interview with People. According to Philipps, she's not opposed to the idea itself as much as she is to the execution. "I'm all for what people want to do in their home," she admitted, "but I need my bed."

Philipps' take-things-as-they-come approach extends to her willingness to let her children make their own decisions — even if they're not always the correct ones. "Are you going to make mistakes? Of course, everyone makes mistakes," she told Yahoo! Life. "But are you going to double down and dig your heels in and let those mistakes define you, or are you going to learn from them and move on?"

Like many actors, Busy Philipps has ventured to the other side of the camera to direct. Her directing credits to date consist of a music video for singer Tomberlin, and a 2015 episode of sitcom "Cougar Town," in which she starred opposite Courteney Cox. "That was really exciting, scary, and a lot of work. But I loved it," she told Backstage about making her directorial debut.

That "Cougar Town" directing experience went so well, she told Insider, that she became eager to take on more directing projects. An opportunity arose when an actor friend, who happened to be starring on a TV show produced by reputable studio that aired on big network, connected her with an executive to discuss the possibility of her directing an episode. "And I was just told like, 'No, it's just not going to happen. The studio won't approve it, the network won't approve it. It's not going to happen,'" she recalled.

In Philipps' estimation, the issue wasn't her relative inexperience, but the fact that she was a woman. "Meanwhile, obviously any dude who's spent 10 minutes on a television show manages to parlay their career into directing," she said, referencing the numerous male actors who segued into becoming directors. "Some of that stuff I think post 'Me Too' has hopefully shifted, but I remember having that meeting with the executive and being really disheartened by his response."

Having her talk show pulled out from under her and then taking things into her own hands with the launch of her podcast, Busy Philipps had reached a point where she was pretty much ready to throw in the towel on pursuing acting gigs. The few offers she was getting, she conceded during an appearance on "The Last Laugh" podcast, weren't exactly creatively fulfilling. "Like, oh, three lines as Jennifer Garner's best friend?" she scoffed.

Then, an unexpected offer came out of the blue when Tina Fey called her up to see if she'd be interested in a TV show she was producing, "Girls5eva," about a one-hit-wonder girl group from the 1990s who reunite years after calling it quits. When she first heard the premise, she told Australia's Nine.com, "I was like this is the perfect confluence of all of these things that I really feel strongly about ... so it was such a dream come true."

As Philipps pointed out in an interview with Variety, "Girls5eva" both satirizes and highlights the casual misogyny within the music industry that was seen as par for the course two decades ago but now seems appalling. "Now everyone is kind of collectively looking back at how women — specifically women in pop music — were treated at that time," she observed. "Everyone rightfully is sort of horrified and feels a great deal of shame."

After decades living in Los Angeles, Busy Philipps — now the newly single mother of two after separating from her husband — made a big move. "We sold our home in Los Angeles and moved cross-country during the pandemic," she told Oprah Daily in May 2022, revealing she had relocated to the Big Apple. "We've been very nomadic since then, renting in different places," she explained. 

Revealing that she and her daughters had recently moved into a new place, she said she was in the midst of turning the house into their home. This, she pointed out, was no mean feat, given that she's the kind of person who only feels at home when surrounded by familiar things. "I'm like the opposite of Marie Kondo," she joked, explaining why she tends to hold onto stuff. "Everything sparks joy for me. And if it doesn't spark joy in that moment, I'm like, well, I have to hold onto it because it might spark joy in three months."

Interestingly enough, Philipps had never lived in New York before. As she told The Daily Front Row, she and her daughters were visiting the city, when she received that fateful phone call from Tina Fey about "Girls5eva," which filmed in NYC. "We stayed and it kind of snowballed — our kids love it and are thriving," she said. 

In 2017, Busy Philipps began experimenting with Instagram Stories, a feature allowing the user to post photos and videos that, unlike regular posts, disappear after 24 hours. "I was an out-of-work actress, and being out of work coincided with of the start of Instagram Stories, and I've always loved reality shows and confessionals ... so I was like, why not make this my own reality show?" she told "Good Morning America." "I didn't care if anyone watched."

But they did. The videos she made for her own amusement began attracting a growing fanbase as she gained more and more followers. In fact, it wasn't long before The New Yorker inquired about a profile focusing on her success with Instagram Stories — something she initially thought was a joke. "But the writer said, 'Every social platform has an early adopter, and you're it for Instagram Stories.' I was like, 'How cool!'" she told Glamour. Meanwhile, the timing was kind of perfect; she'd just finished pouring her heart and soul into a TV pilot that didn't get picked up, leaving her career at a particularly low ebb. Realizing that being noticed for becoming a social media star was better than not being noticed at all, she decided to lean into it. 

"So on my Instagram, I'm playing a version of myself, but it's really important for me to always be truthful with it," she further explained to the Independent.

Given that Busy Philipps' social media success didn't go unnoticed, she was able to parlay her heightened profile into some other projects. One of these was her memoir, "This Will Only Hurt a Little." Published in 2018, the book made headlines for such candid revelations as her fraught relationship with James Franco on the set of "Freaks and Geeks," her struggle with postpartum depression, the rampant misogyny she encountered throughout her acting career, and enduring a horrific sexual assault. 

Having landed her book deal without having to provide a treatment, Philipps told "Off Camera with Sam Jones," she worried that what she'd turned in wasn't what her editor was expecting. "I think that maybe her idea initially of what it was gonna be was probably more a light-hearted romp through Hollywood, and Instagram, and being a mom, and Instagram Stories," she said. 

However, once Philipps began writing she realized she was compelled to tell the whole story, warts and all. Sure, she'd regale readers with fun celebrity anecdotes, but she also decided to pull no punches by recounting the harsher things she'd experienced within the dark underbelly of Hollywood. "I am a very candid person, so when I decided to make the leap and write the book, there was no choice for me but to be as honest as I could be," she explained in an interview with Refinery29. 

If you or anyone you know has been a victim of sexual assault, help is available. Visit the Rape, Abuse & Incest National Network website or contact RAINN's National Helpline at 1-800-656-HOPE (4673).

Busy Philipps first worked with Tina Fey in "The Sackett Sisters," a 2017 comedy pilot for NBC that didn't get picked up. Their association continued, with Fey becoming executive producer of Philipps' short-lived talk show, subsequently hiring her as a guest star in "The Unbreakable Kimmy Schmidt," and then as a series regular in "Girls5eva." In 2023, news emerged that Philipps had joined another of Fey's projects, the much-hyped movie version of the Broadway musical "Mean Girls," based on the beloved 2004 movie for which Fey co-wrote the screenplay. Philipps had been cast as Mrs. George, the "cool mom" played by Amy Poehler in the original film.

Philipps commented on the casting news on — where else? — Instagram. "You know something? I really never have been a regular mom," she wrote in the caption, posting a screenshot of the Deadline story and adding the hashtag #meangirls.

Interestingly, Philipps has an even earlier association with the "Mean Girls" musical. Back in 2019, she and Fey appeared in a brief video promoting the play. While discussing what elements go into crafting the ideal "burn book," Philipps asked Fey what could be written to burn her. Fey, however, was reluctant to go down that road; the best burn she could come up with for Philipps was, "We get it, you're tall."

Most actors tend to be recognized by fans for one or more of their various projects. Given Busy Philipps' vast and eclectic career, which has included roles in film and television, along with her talk show, podcast and popularity on social media, which of her many projects do fans most associate with her? 

"People's frame of reference for me varies ... you know, people get really excited to see me, and it's always for a different project," she explained in a video for Heat, in which she answered fans' questions. "I would say that of all the things I've done — 'Freaks and Geeks,' 'Dawson's Creek,' you know, I was on 'ER' even, the different movies I've been in, 'Cougar Town,' now 'Girls5eva,' my late-night talk show — the thing that I get stopped on the street the most for is 'White Chicks.'"

Philipps looked back at her role in the cross-dressing comedy while appearing on the "Absolutely Not!" podcast. "You do know that I played the fat girl in 'White Chicks,' that's what my character was described as," Philipps said, suggesting the humor in the 2004 movie is far too politically incorrect for modern audiences. "To be totally honest with you, I think I was a size 8 ... Upon further reflection, maybe that was the joke, that she wasn't really fat but that they are just so horrible ... That movie wouldn't be made now."