Age is more than a number to Ally Sheedy. It’s how she remembers the most significant moments of her life. Nineteen is when she did her “first real movie,” Bad Boys with Sean Penn. Twenty-nine is the year she got married. At one point during our recent conversation, she even asks my age. When I sheepishly reply that I’m in my 20s, she says, “No, that makes me so happy, actually. You’re the age of my son.” Now, at age 59, Sheedy’s back in the spotlight with Single Drunk Female—her first major onscreen role in more than five years. 

It’s a moment that she isn’t taking for granted. “I’m so grateful, but also I’m so relieved,” Sheedy tells me. “I just did not know if another role that would resonate this much within me would come again.” 

“Again, remember I’m 59. So during my 50s, I just thought, Hmm, I’m really going to miss acting. I love it so much. It’s heartbreaking not to do it more, but I can do this, I can do that. I have other things. I wasn’t expecting this. Then it showed up.”

This is Freeform’s breakout new comedy from creator Simone Finch, and a creative team that includes writer-producers Jenni Konner (Girls) and Leslye Headland (Russian Doll). The show stars Sofia Black-D’Elia as Sam, the titular unattached alcoholic. “This was absolutely the group of people, especially the group of women, that I really have always wanted to work with,” Sheedy says. “So when it showed up, I thought, Oh, God, great. I want to go back to work.”

Sheedy plays Sam’s mother, Carol, whose approach to sobriety is complicated. In some moments, Carol is loving and supportive of her daughter’s recovery. At others, their dynamic is soured by Carol enabling Sam’s addiction. “I know that alcohol and drinking is the major theme here, but for me it wasn’t,” Sheedy explains. “The first reaction I had reading the script was, Oh, my God, it’s Terms of Endearment, which is probably my favorite movie, mainly because of Debra Winger, Shirley MacLaine—what they did with that writing and the way that relationship unfolded during that movie. I think it’s so brilliant and so edgy and just timeless.”

Another touchstone for Sheedy has been director Travon Free, who won an Oscar for his 2020 live-action short film, Two Distant Strangers. Free directed two of Carol’s most pivotal episodes—a collaboration she’s grateful for. “He’s so insightful about actors and character and writing. He is probably my most favorite director of all time,” Sheedy says. 

Their bond was solidified in the show’s recent ninth episode, in which Carol and Sam’s relationship has frayed at both ends. After Sam fails to invite her mother to her first sobriety anniversary, she attempts to make amends. But Carol quickly deflects, pivoting into an impromptu ash sprinkling for her late husband, Sam’s father. In any other show, this ceremonial act would be sentimental—but not in Single Drink Female. “The [appearance of the] ashes have to be not ‘Ugh, let’s also take a wreath and send it out over the water,’” Sheedy says. “It was just, Okay, here’s a ritual that we should do. As far as Carol’s concerned, she feels like I should do this ritual with my daughter because it’s time. But there’s not that much extra on it. And it’s anticlimatic.” 

Free also helmed the show’s fourth episode, in which Carol explains to her boyfriend, Bob (Ian Gomez), why she’s resistant to sex. At one point, Bob asks Carol what he can do to make her more comfortable. “Make me 30 years younger,” she tearfully tells him. It’s a moment that seems to come from a deep place for Sheedy. “[This] is not something that anyone usually even talks about—[being] postmenopausal, having an intimate sexual encounter with a person, just basically the most scary thing that Carol could imagine,” she says.

As written, the line could’ve been played for laughs. But in the hands of the right director, Sheedy could deliver it with full weight. “I just said, ‘I don’t think this is a joke. I don’t think saying, ‘make me feel 30 years younger’ is a joke. I think it’s real,’” she remembers telling Free. “And he said, ‘You’re right. Go for it.’ And so I had this day of kismet, you know what I mean? It doesn’t always happen.” The moment gets more layered when one remembers that it’s coming from the same actor who uttered one of The Breakfast Club’s most enduring lines three decades ago: “When you grow up, your heart dies.” 

Sheedy says that any parallels between Carol and herself—a woman who’s routinely asked about what she was doing 30 years ago—only arrived after filming. “I wasn’t at the moment thinking about myself, except myself at 59 as opposed to 29, right? But then later I thought, wow, it’s so interesting—because yeah, 30 years younger for Ally, for me as a person in the TV-film world, actually has another angle into it,” she says. “I’ve been asked about the scene a few times by people, and I feel ‘oh, it reverberated.’ But it only did because Jenni wrote it, and then Travon let me do it that way instead of it being a throwaway line.”

Sheedy, who skyrocketed to fame with a string of major roles in the ’80s—WarGames, St. Elmo’s Fire, Short Circuit—has a newfound appreciation for her Brat Pack–adjacent adolescence. “My 20s were maybe not like other people’s 20s, but [also] kind of not that different,” she says. “Movies and working in film and TV and all that—it was this all-consuming love affair in my 20s. This is what I want to do…. So I understand myself in my 20s, and I also understand how dangerous it can be to simply decide this is my path—period, end of story, nothing else matters. But that’s in your 20s. You’re passionate.”

In the years since, Sheedy’s allowed her passions to ebb and flow elsewhere. “In your 20s, it feels like I have this one thing that I love, my purpose,” she says. “But actually there are branches that can come off from that, that can really expand your life and are part of the same thing but bring other stuff in. I didn’t know that in my 20s.” 

For the last decade, Sheedy’s extended her branches into teaching and editing. She’s a professor in the theater department at City College of New York, and a book editor under a pseudonym. (“Some of them know that it’s actually me working with them and their books, and a whole bunch of them don’t.”) Both have offered Sheedy “fulfillment that’s actually completely different from the joy I get out of acting.”

It’s always been a gradual retreat from the limelight, one that began percolating after the birth of her son, Beckett, in 1994. “I remember thinking, I’m really tired of thinking about myself all the time,” Sheedy says. “I need my life to be about something else. And someone else.” That idea was interrupted, however, by 1998’s High Art, in which she plays a drug-addicted photographer—a performance that won her an Independent Spirit Award. 

It’s a film that Sheedy thinks could be due for rediscovery. “My favorite film, I actually think it’s High Art,” she says. “I love the writing. I love the cast. I love Patricia Clarkson, Radha Mitchell. Maybe it doesn’t work, maybe it’s a little dated right now. But it’s my favorite role, besides Allison [from The Breakfast Club] and Carol. Those are the three roles that I just feel like I’m so lucky to have had, and cement what I’ve been doing over the decades.”

— Jerry Lewis’s Costars Speak Out: “He Grabbed Me. He Began to Fondle Me. I Was Dumbstruck”
— Inside Charlize Theron and Tom Hardy’s Mad Max War
— Inventing Anna Is a “Dangerous” Distortion, Says Rachel Williams
— How the Gun in Alec Baldwin’s Hands Turned the Rust Set Deadly
— Love Is Blind Season Two Is Peak Red Flag Television
— Pachinko First Look: An Epic Tale, and a History-Making Show
— Vanity Fair’s Hollywood Issue 2022: See the Full Portfolio Featuring Nicole Kidman, Kristen Stewart, and More
— The Ugly Truth of How Movie Scores Are Made
— Kirsten Dunst on Her First Oscar nomination for The Power of the Dog
— From the Archive: With Friends Like These
— Sign up for the “HWD Daily” newsletter for must-read industry and awards coverage—plus a special weekly edition of “Awards Insider.”