Unbreakable Bond: The Unforgettable BFF Moments of Michelle Williams and Busy Philipps

The love triangle between Joey, Pacey, and Dawson on Dawson's Creek may have captured the hearts of fans for years, but it's the real-life friendship between Busy Philipps and Michelle Williams that has truly stood the test of time. Their bond first formed on the set of the popular teen drama when Williams portrayed Jen Lindley for three seasons and Philipps joined as Joey's college roommate, Audrey Liddell, in the fourth season. From the moment they met, their connection was undeniable, and over two decades later, the two women continue to be an important presence in each other's lives.

Throughout the years, the Busy Tonight alum has been a constant companion to her best friend on red carpet events, consistently expressing her immense pride in the Oscar nominee.

"In September 2020, on Williams' 40th birthday, we reminisced over our 20-year friendship - a friendship that defies logic as we still feel as if we're merely 27," Philipps jested on Instagram. "I truly yearn to be by her side tonight, celebrating her exceptional, brilliant nature. I want to personally convey my eternal gratitude for crossing paths all those years ago, for she is the one I want to face any challenges with and revel in all the joys together. We've shared countless tears, laughter, and moments of indulgence and restraint."

The Cougar Town alum expressed her excitement for growing old with her friend and envisioned a future of visiting farmers markets in the countryside. She imagined herself with long grey hair, neatly pulled back in a bun, while her friend Michelle wore a large sun hat to protect her flawless porcelain skin. In an exclusive interview with We in January 2021, Philipps shared her and Williams' cherished awards season tradition of having post-show breakdowns.

"After every awards show, everyone would say, ‘Oh, it's always great to see you both together at these events.’ We often find ourselves back in her hotel room, you know, since she doesn't live in Los Angeles, and we just unwind together,” shared the Girls5Eva star.

Philipps added that the women would remove their extensions, change into comfortable clothes, and relax before heading out to eat at Jon & Vinny’s. “We kind of embody a classic elegance, like glamorous old ladies, but without the cigarettes because none of us smoke,” she quipped.

In May 2021, the host of the "Busy Philipps Is Doing Her Best" podcast expressed openness to collaborating with Williams again in the near future. The pair previously worked together in Amy Schumer's film "I Feel Pretty" in 2018. Philipps shared that the opportunity to work together had aligned effortlessly due to her then-husband, Marc Silverstein, directing the project. She also hinted at the possibility of Tommy Kail, who is a director as well, helming a project for both her and Williams.

Scroll to see the friends’ cutest joint appearances of all time:

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Michelle Williams and Busy Philipps' Best BFF Moments Over the Years

The love triangle between Joey, Pacey, and Dawson on Dawson's Creek continues to captivate fans even decades later. However, what really has fans buzzing is the incredible friendship between Busy Philipps and Michelle Williams, which blossomed on the hit teen drama.

Michelle Williams portrayed Jen Lindley on the WB series for three seasons, and it was during the fourth season that Busy Philipps joined the cast as Audrey Liddell, Joey's college roommate. From the moment they shared the screen, their chemistry was undeniable. And now, over 20 years later, these two remarkable women remain an integral part of each other's lives.

Over the years, the former Busy Tonight cast member has accompanied her closest companion on the glamorous red carpet and consistently expresses her admiration for the talented Oscar nominee.

“We crossed paths two decades ago, which defies logical explanation since we both still look like we're only 27,” Philipps playfully shared on Instagram in September 2020, honoring Williams on her 40th birthday. “I genuinely wish I could be present tonight, celebrating the sheer uniqueness and immense brilliance she possesses. I want to personally convey my eternal gratitude for our fateful meeting all those years back. There's no one else I would prefer to navigate life's challenges with, to revel in all the amazing things, to shed tears of both joy and sorrow, to share laughter that echoes through the air, to partake in drinks or abstain altogether."

The former star of "Cougar Town" expressed her excitement about growing old with her friend. She envisioned the two of them going to farmers markets in the countryside. She imagined herself with long grey hair, neatly parted in the middle and pulled back in a bun, while her friend would wear a large sun hat to protect her flawless porcelain skin.

In January 2021, Philipps shared with We Magazine their favorite ritual during awards season - the post-show breakdown.

"After every awards show, there is always the usual excitement from everyone, expressing their delight at seeing us attend the events together. It has become somewhat of a tradition for us to reconvene in her hotel room afterwards. You see, she doesn't reside in Los Angeles, so it just makes sense for us to unwind together in a familiar setting," shared the Girls5Eva star.

Philipps playfully mentioned that during these casual hangouts, the ladies remove their hair extensions and change into comfortable clothing, embracing a sense of relaxed elegance. Their choice of dining at Jon & Vinny's adds to this laid-back atmosphere. "We embody a certain old-fashioned glamour, except without the cigarettes, as neither of us are smokers," she jokingly added.

In a recent interview with Us, the "Busy Philipps Is Doing Her Best" podcast host revealed that she is open to the possibility of collaborating with Williams again in the near future. The talented pair previously worked together in Amy Schumer's 2018 film, I Feel Pretty. Philipps shared that the opportunity arose because her then-husband, Marc Silverstein, was directing the film. Now, with Michelle and Tommy Kail also having directing experience, there is a chance for them to come together for another project.

Scroll to see the friends’ cutest joint appearances of all time:

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A Busy-Less Oscars

In March 2023, Philipps took to her Instagram Story to express her disappointment at not being able to be present with her best friend during her nomination. However, being in New York at the time, she was determined to find a way to watch the event. Despite not being physically there, Philipps still managed to praise her friend's impeccable red carpet look during the pre-show. Unfortunately, Williams did not take home the Best Actress trophy, as it went to Michelle Yeoh instead. Nonetheless, Philipps reassured her friend that she would be by her side when she finally wins an Oscar. This nomination marked Williams' fifth time being recognized for her outstanding performance in The Fabelmans.

"Listen, when Michelle's sixth nomination [happens], it's gonna be the one. I'm gonna be with her. She's gonna win," Philipps shared with her Instagram followers.

Credit: Courtesy Busy Phillips/Instagram

Celebrating Success

Philipps took to Instagram in March 2023 to celebrate her close friend Kail for his exceptional work on the "spectacular" Broadway production of Sweeney Todd. Instead of sharing a blurry photo of herself and Michelle taken after the show, Philipps decided to treat her followers with a picture taken at the Critics Choice Awards by Myles Hendrik. "I couldn't post the weird blurry picture Michelle and I took together last night after @sweeneytoddbway so instead, please enjoy this pic @myleshendrik took of us at the Critics Choice Awards!" she humorously captioned the photo.

Credit: Evan Agostini/Invision/AP/Shutterstock

So Deserved

Philipps expressed her heartfelt congratulations to her former costar from Dawson's Creek on her well-deserved Best Actress Oscar nomination for her remarkable performance in The Fabelmans. Sharing a nostalgic throwback photo of Williams on Instagram, the beloved actress wrote, "BRB- I'm just gonna go back in time and tell this kid that she's going to have 5 OSCAR NOMINATIONS in the next 20 years. And a BEAUTIFUL family. And be surrounded by love. (And GORGEOUS CLOTHES). But tbh- that's probably along the lines of what I was saying to her then. I love you MW."

Philipps continued her heartfelt message, expressing her everlasting pride in Williams for building the life and career she had always dreamt of, despite grappling with the overwhelming grief that comes with being human. She acknowledged Williams' unwavering determination to rise above the challenges, stating, "But then you would dig deep and try again. It's one of my favorite things about you. You have never NEVER stopped trying. A new way, a new recipe, a new parenting style, a new author, a new approach to work, a new love, a new role...but always the same loving brilliant gentle sensitive funny wild thoughtful beautiful beautiful BEAUTIFUL you. ❤️."

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Date Night

The Fabelmans star and Philipps posed together on the 2023 Critics’ Choice Awards red carpet.

Credit: Gregory Pace/Shutterstock

Jen and Audrey

Philipps accompanied Williams to the Gotham Awards in November 2022, where they witnessed the Fabelmans star deliver a heartfelt tribute to their former costar, Mary Beth Peil, during her acceptance speech.

Sharing her experience on Instagram, Philipps expressed her gratitude for being Williams' date and described Paul Dano's moving speech about Michelle as an artist, a person, and a mother, which brought her to tears. Philipps also praised Williams for taking the opportunity to honor Mary Beth Peil, who had greatly impacted her life and career. Although Mary Beth was unable to attend the event due to illness, Philipps wished she could have been there with them.

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Perfect Project

In a lighthearted exchange, Philipps playfully revealed that there was a special condition that would entice her to collaborate once more with Williams. The duo had previously appeared together in the film I Feel Pretty, but now, three years later, Philipps teased that there was an enticing factor that could potentially bring them back together on screen.

"It all came together seamlessly because my ex-husband, Marc Silverstein, was at the helm of the project," she revealed to Us in an exclusive interview, before playfully suggesting that Thomas Kail, Michelle Williams' husband, could potentially take charge of their future collaboration. "Tommy is also a talented director, perhaps we can entice him to direct a project for the two of us."

Credit: Jordan Strauss/Invision/AP/Shutterstock

Pandemic Pros

The Freaks and Geeks alum revealed in May 2021 how her relationship with the Blue Valentine star has evolved during the COVID-19 pandemic. Despite feeling closer in some ways, they have faced challenges in being physically together and embracing the same level of intimacy. To continue with her work commitments, Philipps moved from L.A. to New York to film Girls5Eva, which allowed her to be in the same city as Williams.

Fortunately, towards the end of 2020, the two were able to reunite after maintaining distance due to social distancing measures. Both families went through a quarantine period and ultimately spent quality time together during the holiday break. This experience brought immense joy to Philipps, who expressed her excitement and gratitude for being geographically close to Williams now.

Credit: Courtesy of Busy Philipps/Instagram

Awards Season Ritual

"Following any awards show, there is always a buzz about seeing us together," Phillips exclusively shared with us in January 2021, referring to her customary awards season routine with Williams. "We inevitably find ourselves back at her hotel room since she doesn't reside in Los Angeles. It's there that we unwind together," she continues. "We remove our extensions, delicately take off our false eyelashes, thoroughly cleanse our faces, and slip into comfortable sweatpants and cozy attire. Afterward, we usually indulge in a meal at Jon & Vinny's or grab some food elsewhere. We exude a certain timeless elegance, reminiscent of old Hollywood glamour, but without the cigarettes, as neither of us are smokers."

Credit: Jordan Strauss/Invision/AP/Shutterstock

Golden Friendship

The 2020 Golden Globes saw the former host of Busy Tonight gracing the event. Alongside her was her best friend, who received a nomination for Best Actress in a Miniseries or Motion Picture Made for TV for her role in Fosse/Verdon. Adding to the joyous occasion, Williams attended the awards ceremony with her fiancé, Thomas Kail, as they eagerly await the arrival of their first child.

Credit: Courtesy Busy Philipps/Instagram

NYC Reunions

Exploring new places becomes all the more special when you have friends by your side! In a delightful instance, Philipps captured a mirror selfie with a dear friend in December 2019 when they got together in the vibrant city of New York for a memorable evening. Such moments of togetherness create cherished memories that last a lifetime.

Credit: Christopher Polk/Variety/Shutterstock

Support System

Philipps arrived as Williams’ date at the 2019 Emmy Awards in September. Williams was nominated for Lead Actress in a Limited Series or Movie for Fosse/Verdon.

Credit: Busy Philipps/Instagram

Liquid Courage

In an October 2017 Instagram Stories series, Busy Philipps and Michelle Williams joyfully opened a bottle of white wine and embarked on a hair dyeing adventure. The duo documented the process as Philipps carefully transformed Williams' hair into the ideal shade of pink!

Credit: Busy Philipps/Instagram

Sleeping Beauties

In October 2017, Philipps and her companion took a moment to capture their exhaustion in a photograph, as they lounged on plush pillows. Reflecting on their exhilarating four days in Paris, she playfully commented, "We're tired. Thank you Paris for an exhausting and exhilarating four days. I would say I'm going to now sleep for four days but I have kids so that's OBVIOUSLY not gonna happen."

Credit: Stephane Cardinale - Corbis/Corbis via Getty

Fashion For Two

Philipps and Williams attend the Louis Vuitton show together during Paris Fashion Week in October 2017.

Credit: Busy Philipps/Instagram

Where My Ladies At?

In October 2017, Philipps and Williams made an unconventional move by bringing the Fashion Week party into the ladies room. Within this intimate setting, Williams can be witnessed receiving a touchup, while Philipps captures a mirror selfie featuring the entire group.

Credit: Pascal Le Segretain/Getty

The Yin To Her Yang

The duo brought the perfect balance of colors to the opening of the Louis Vuitton Boutique in Paris during Paris Fashion Week in October 2017. 

Credit: Courtesy Busy Philipps/Instagram

Jen and Audrey Forever!

In September 2017, the group of friends gathered together and fondly remembered their time on the hit TV show Dawson's Creek. One of the cast members, known for her role in Cougar Town, shared a nostalgic photo on Instagram. The caption humorously referenced a famous line from the show, with a twist, as she playfully asked, "WHERE YOU AT DAWSON? #wedontwanttowaitforourlivestobeover."

Credit: Busy Philipps/Instagram

Best Friends Forever

In September 2017, Philipps shared a heartwarming post on her Instagram account featuring a picture of herself and Williams donning matching leather jackets, symbolizing their unbreakable bond of friendship. Alongside the photo, she expressed her heartfelt birthday wishes, affirming that Williams was her perfect companion and dearer half. With a touch of affection, Philipps concluded her message by declaring her profound love for Williams, emphasizing how she brings positivity and brightness into every aspect of their lives.

Credit: Kevork Djansezian/Getty

These Two!

Williams brought Philipps as her plus one to the 89th Academy Awards in February 2017, when she was nominated in the Best Supporting Actress category for Manchester by the Sea.

Credit: Christopher Polk/Getty

Busy Bees

The former Dawson's Creek costars shined at the 23rd Screen Actors Guild Awards in L.A. in January 2017.

Credit: Neilson Barnard/NBCUniversal/NBCU Photo Bank via Getty Images

Golden Girls

In Louis Vuitton (Williams) and Stella McCartney (Philipps) at the Golden Globes in January 2017.

Credit: Astrid Stawiarz/Getty

By Her Side

At the Louis Vuitton–hosted screening of Manchester by the Sea on December 2016.

Credit: Steve Granitz/WireImage

Ladies in Lace

At the 22nd Annual Critics' Choice Awards in December 2016.

Credit: Larry Busacca/Getty

Case of the Giggles

In a slitted Louis Vuitton dress (Williams) and floral Ingie Paris (Philipps) at the Tony Awards in June 2016.

Credit: Jeff Kravitz/FilmMagic

Hand in Hand

At the Oscars in February 2012 (the year Williams, in Louis Vuitton, was nominated for Best Actress for My Week With Marilyn).

Credit: George Pimentel/WireImage

Babes in Blue

At the Film Independent Spirit Awards in February 2012.

Credit: Jeff Vespa/Getty

Say Cheese!

In blue velvet Jason Wu (Williams) and fringed Temperley London (Philipps) at the 69th Annual Golden Globe Awards in January 2012.

Credit: Kevork Djansezian/Getty Images

Heart Eyes

In beaded Chanel (Williams) and Douglas Hannant (Philipps) at the 2011 Oscars in February 2011.

Credit: Frazer Harrison/Getty

Printed Pals

At the Weinstein Company's 2011 Golden Globes afterparty in January 2011.

Credit: J. Vespa/WireImage

Oscars Mugging

With Williams, nominated for Best Supporting Actress for Brokeback Mountain, in her iconic marigold Vera Wang gown at the Academy Awards in March 2006.