Molly Shannon’s 25 Best Roles, Ranked

Photo-Illustration: Vulture; Photos by Netflix, HBO, Columbia Pictures, Fox 2000 Pictures, Universal Pictures and Paramount Pictures

Molly Shannon is currently having a moment — one that is long overdue, and we’re all lucky to be along for the ride. Fresh off her scene-stealing role in The White Lotus, the SNL alum is currently taking center stage in the long-awaited second season of HBO Max’s The Other Two. Next year, we’ll get to see even more of Shannon on our screens with her role in Vanessa Bayer’s Showtime series, I Love This for You, as the star host at the home-shopping network that Bayer’s character dreams of working at. And in April, she will release a memoir, Hello, Molly!, which hopefully will include the written account of the Greatest Story Ever Told™, a.k.a. when she snuck onto a flight to New York at 12 years old.

Whereas most of her Saturday Night Live peers found their way to the show by way of the Second City or the Groundlings, Shannon landed there after putting on her very own stage show, feeling like casting directors just weren’t “getting it” in her auditions. When she made it to SNL, everybody got it, and the prolific performer churned out an endless parade of instantly iconic characters. Since then, she has become an expert in making meals out of even the smallest of supporting roles or guest appearances across film and television — stealing the show more often than not.

Her dramatic turns demonstrate her unparalleled range, flipping between deeply grounded to slapstick physical comedy with ease. From Sally O’Malley to Emily Dickinson, whether she’s throwing herself through bathroom-stall walls or shattering hearts as a mother dying of cancer, Shannon can do it all. So let’s look back at 25 of the legend’s best performances, big and small.

25. Fun Mom Dinner (2017)

In what seems like an aftershock of the Bad Moms Cinematic Universe, Fun Mom Dinner features Shannon in an all-too-rare lead role alongside an exceptional cast that makes the most of this light romp’s fairly thin script. Truth be told, the entire 82 minutes could have consisted of Bridget Everett leading the quartet of moms in their karaoke performance of “99 Red Balloons” (in both German and English) and I would have been just as happy, if not more so. Nonetheless, it’s still a joy to see the always underused Shannon and Everett lead this film along with Toni Collette and Katie Aselton, and to paraphrase Liza Minnelli’s thoughts on Renée Zellweger’s Judy, “I hope they had a good time making it.”

24. Serendipity (2001)

No funny female (or gay male) character actor’s filmography is truly complete without a turn as the best friend in a rom-com, and in Serendipity, Shannon did just that, playing confidante to Kate Beckinsale’s superstitious Sara. Her character is dragged along on, and then unintentionally facilitates, Sara’s mission to track down her serendipitous love interest in New York. Though the script doesn’t give her too much to do, Shannon manages to stand out with a golf-club-induced pratfall and an alliterative line reading of “Good-bye, my sweet lesbian lady lover!” (More on Emily Dickinson later.)

23. Life After Beth (2014)

Shannon has become a regular player in writer-director Jeff Baena’s films, appearing in Horse Girl, The Little Hours, and Life After Beth, typically in a maternal supporting role. Though Baena (husband to Aubrey Plaza and brave survivor of David O. Russell’s I Heart Huckabees) helmed all three, the psychological thriller, nun comedy, and zombie flick, respectively, couldn’t be more different. The latter gives Shannon the most to do, playing the mother of a girl (Plaza) who comes back to life as a zombie — or as she forcefully maintains in an attempt to stay positive, her daughter has simply been resurrected.

22. Marie Antoinette (2006)

Marie Antoinette is a departure from Shannon’s usual fare, not just because she’s taking on the role of a historical figure in a period piece but because the character is much colder than we’re used to seeing from Shannon. She takes on the role of the gossipy Aunt Victoire to Kirsten Dunst’s Marie Antoinette, serving up a cross between Cinderella’s stepmother and Regina George — particularly in one scene when she compliments Marie’s outfit moments before criticizing someone else’s behind their back. An “ugliest effing skirt” moment, but in 18th-century France.

21. The 2018 Rose Parade Hosted by Cord & Tish (2018)

In 2018, Will Ferrell and Shannon hosted Amazon’s broadcast of the Rose Parade in character as fictional broadcasters Cord Hosenbeck and Tish Cattigan — just for fun. Their straight-faced two-hour bit resulted in a swarm of angry reviews from people who simply wanted to watch the Rose Parade and never caught on to the bit. At one point, over 60 percent of the Amazon reviews were one star, earning comments like “Horrible. I wanted to hear one of the local bands, but the unfunny hosts were babbling some nonsense about omega-3’s and salmon … what?” and “The two [hosts] need to be placed in a psych ward somewhere.” The pair reunited for another Rose Parade and to cover Harry and Meghan’s royal wedding, but it’s clear the duo should be hosting everything from the Macy’s Thanksgiving Day Parade to the Oscars red carpet.

20. Bob’s Burgers (2013–21)

For a woman who is so animated in real life, Shannon is obviously a natural for literal animation. She’s had several guest appearances on Bob’s Burgers as Millie, a fourth-grader who is obsessed with befriending Louise Belcher, much to Louise’s horror. Shannon delivers a hauntingly maniacal cackle in the role, and at a pitch slightly higher than her normal voice, it might take viewers a moment to identify her. She is clearly a pro, having also lent her voice to films like Igor and the Hotel Transylvania series, but Pixar really should be in touch.

19. Promising Young Woman (2020)

At the turning point of Promising Young Woman, Carey Mulligan’s Cassie pays a visit to her late best friend’s mother, played by Shannon. It’s a small yet pivotal role, in which she encourages Cassie to stop her revenge mission, telling her that nothing can ever set right what happened to her daughter. The role could have been played any number of ways, but Shannon walks a fine line between being comforting toward Cassie but also very firm in her insistence that she stop her ill-fated quest for retributive justice. There isn’t a good-bye hug when Shannon gets up from their conversation, just a closed door.

18. How the Grinch Stole Christmas (2000)

In Ron Howard’s Dutch-angle-filled take on the Dr. Seuss classic, Shannon plays the mother of Cindy Lou Who, but even more important, her character is the decorating rival of Christine Baranski’s Martha May Whovier. Shannon’s Betty Lou Who frantically covers their Whoville home with Christmas lights, from the refrigerator bulb to a torn-down traffic light — an iconic agent of chaos. Filmed at the same time as Serendipity, Shannon would show her co-star Beckinsale (who, much like the rest of the world, describes Shannon as one of her favorite people to ever exist) a photo of her complex Grinch prosthetics whenever she’d complain about being tired.

17. Me and Earl and the Dying Girl (2015)

Shannon plays the wine-clutching mother of the dying girl in question in this film based on the young-adult novel of the same name. It’s a movie that at times is deeply sad (like when they waste Connie Britton’s hair by styling it up the whole time) but more often darkly comedic — usually courtesy of Shannon’s boozy, overly affectionate character who offers her daughter’s teenage friends just “a little taste” of wine and sits like Sharon Stone in Basic Instinct for an interview about her daughter.

16. Never Been Kissed (1999)

As the flirty Anita in this classic Drew Barrymore rom-com, Shannon doesn’t just steal the show as Josie’s work confidante but gets an iconic scene of her own in the middle of the film when she attempts to visit her colleague’s undercover operation. Mistaken as the sex-ed guest speaker, Anita gets roped into addressing Josie’s high-school class on the subject, delivering the classic line, “Sex, um, what do you say, really? You like a guy, you do it with him. Sometimes he calls; sometimes he doesn’t!”

15. Private Life (2018)

In this Tamara Jenkins film, Kathryn Hahn and Paul Giamatti play a couple desperate to have children whose 25-year-old niece, Sadie, offers to be their egg donor. Shannon plays Sadie’s sardonic and judgmental mother who forcefully protests this decision — storming out of Thanksgiving due to the announcement and furiously taking an electric carver to the turkey. Her displeasure doesn’t just drive the story’s conflict; Shannon’s performance also brings levity, like when she is convinced her in-laws have brainwashed her daughter for her eggs or when she summarily says, “No, I’m not cool with it. I’m not cool with anything, ever.”

14. Wild Nights With Emily (2018)

We need an Actors on Actors with Shannon and Queen of Pop Hailee Steinfeld about playing Emily Dickinson. As opposed to Steinfeld’s Dickinson, Wild Nights With Emily explores the poet’s later years, in a tone that more closely resembles a romantic comedy — or even an episode of Drunk History. It delves into the misconceptions and myths surrounding Dickinson, flashing back and forth between the posthumous interpretation of her work and Dickinson’s actual life. It’s not the type of role we typically get to see Shannon in, but for a story that tries to showcase an often ignored side of Dickinson, particularly her humor, she proves to be the perfect fit to humanize the poet. The smart casting is thanks to director Madeleine Olnek, who knew Shannon’s potential, having not only gone to NYU with her, but Olnek directed the college comedy show in which the character of Mary Katherine Gallagher was first conceived.

13. Wet Hot American Summer (2001)

Shannon is just one in the stacked ensemble of Wet Hot American Summer — as well as in the two TV spinoffs, First Day of Camp and Ten Years Later — in which she plays Gail, the morose arts-and-crafts (“Or as we used to call it, arts and farts and crafts”) teacher who is guided through her messy divorce by the group of young children that she confides in. Her delivery of “I do not need you to undermine me” to a small child who suggests using markers is simply unbeatable.

12. Enlightened (2013)

Before The White Lotus made Mike White an HBO darling, he and Laura Dern created the painfully underappreciated Enlightened that ran for two seasons on the network (cue Valerie Cherish’s “Started It all”). In the cult-classic series, Dern’s Amy Jellicoe suffers a nervous breakdown that ultimately leads to her takedown of her corrupt corporate workplace from within. Shannon enters the series midway through its second season as Eileen — a self-proclaimed “learned extrovert” and the secretary of a company executive — who forms a relationship with Jellicoe’s partner in crime, Tyler. Shannon’s Emmy-nominated performance not only provided the perspective of a “company woman” in contrast to Amy’s burn-it-all stance, but it created an internal conflict with Tyler (and, in turn, the viewer) about using the kindhearted, sweet Eileen to expose the company.

11. Will & Grace (1999–2019)

Beginning in the series’ first season, Shannon started making guest appearances on Will & Grace as Val, the titular pair’s crazy upstairs neighbor. Dubbed everything from “wackadoo” to “wingnut,” Val pops up throughout the show’s run to brawl with Grace over Will’s friendship, stalk Jack, and become a kleptomaniac. By just her fourth appearance, continuing through her Emmy-nominated return in the revival, Shannon’s appearance elicited scene-halting cheers from the studio audience. The wacky antics gave Shannon the chance to show off her flawless broad comedy skill set that’s a must for the SNL stage but rarely transfers to other, more grounded projects outside Studio 8H.

10. Radio Andy Theater (2019)

Outside Saturday Night Live, Shannon has only ever played three real people: Princess Victoire of France, Dickinson, and Sonja Morgan from The Real Housewives of New York City. In a live reading of a classic season-11 RHONY episode (“Life Is Not a Cabaret”) for Andy Cohen’s SiriusXM channel, Shannon takes on the role of Sonja alongside brilliantly cast heavy hitters like Bayer as Ramona and Kristen Johnston as Luann. Working from a verbatim transcript for an audience at West Hollywood’s the Peppermint Club, Shannon simultaneously rings true to the original while breathing new life and humor into the sacred text.

9. Talladega Nights: The Ballad of Ricky Bobby (2006)

There’s nobody better at acting drunk than Shannon, who puts that skill on display for every second she appears in Talladega Nights. As the boozy wife of Dennit Racing’s owner, Shannon makes a tiny role unforgettable with lines like, “There’s only one good thing about coming to these races, and that is the vibrations from the cars. I love when them cars whizz by. Oh, feel the motor runnin’ up my leEeEgs,” and by drunkenly greeting a geriatric investor by saying “You have beautiful teeth” and kissing him on the mouth.

8. Saturday Night Live (1995–2001)

Hired as a mid-season replacement for Janeane Garofalo in 1995, and then being one of the only five cast members to survive the following season’s cast overhaul, Shannon spent six years at Saturday Night Live. Those six seasons (at the time, a record for longest-running female cast member) could be a list in and of itself. She tackled real-life figures like Monica Lewinsky and Elizabeth Taylor but really made her mark with iconic characters like Mary Katherine Gallagher, quinquagenarian Sally O’Malley, and licensed joyologist Helen Madden (“I love it, I love it, I love it!”). Looking back, it’s remarkable how well these slapstick roles have stood the test of time, particularly Jeannie Darcy, Shannon’s awkward mullet-sporting and bolo-tie-wearing stand-up character, whose cringe comedy feels before its time. But don’t get me started — don’t even get me started.

7. The White Lotus (2021)

Shannon blazed into The White Lotus four episodes in, absolutely chomping on the end of a pair of sunglasses as her character, Kitty, crashed her son’s honeymoon and closely examined the room she didn’t book. Shannon doesn’t just exude wealth in the role but a deeply lived-in wealth, so much so that any other way of life is incomprehensible to her. Take, for example, her struggle to understand her daughter-in-law’s desire to continue her career, asking “No, why would you do that?” with genuine confusion. Shannon makes the role more complex than a typical rich monster-in-law archetype — with even her tiniest inflections and passive-aggressive barbs informing us about the family’s privilege and the world Alexandra Daddario’s Rachel is getting herself into. Despite only being in two episodes, she was a series standout, so we can only hope that Kitty happens to be vacationing at another White Lotus property in season two. It’s also worth noting that during filming, it was Shannon who told her co-star Lukas Gage that he should post the video of his viral Zoom audition, so we have her to thank for that.

6. The Other Two (2019–)

From former SNL head writers Chris Kelly and Sarah Schneider, The Other Two is about two adult siblings who have to watch on as their 13-year-old brother finds overnight internet stardom. Shannon plays the trio’s mother, Pat Dubek, in a role that easily could have been written as a horrible stage mother for laughs but is instead a character who deeply loves all three of her children and navigates this newfound fame with doe-eyed awe — making her the heart of the show. In the second season, the series takes a shift that centers Shannon’s character as the “famous” Dubek, having now snagged her own talk show. It’s only a matter of time until Shannon’s Pat Dubek hairstyle catches on like “the Rachel” did.

5. The Santa Clause 2 (2002)

There’s no better example of Shannon’s ability to not only steal a scene but an entire film than her less-than-three-minute performance in The Santa Clause 2. Tasked with finding a Mrs. Claus, Tim Allen’s character has to dive into the dating pool, sending him on a blind date with Shannon’s Christmas-obsessed aspiring singer-songwriter Tracy. While serving a master class in wrist choreography featuring her Christmas-charm bracelet, Shannon seamlessly delivers a range of emotion that goes from flirtatious to giddy to embarrassed to furious. Wearing a Santa sweater, she performs an impromptu Christmas parody of Shania Twain’s “Man! I Feel Like a Woman!” in the middle of a restaurant, earning a spot in the holiday canon alongside the likes of George Bailey. It’s a crime that her rendition isn’t performed at the Rockefeller Center tree lighting every year and that carolers aren’t making their way through neighborhoods screaming, “Put up a tree! Sports on TV!”

4. Divorce (2016–19)

Before there was And Just Like That , Sarah Jessica Parker’s big return to HBO was Divorce. From Catastrophe creator and star Sharon Horgan, the show stars Thomas Haden Church and SJP as a divorcing couple, with Shannon as the eccentric friend of Parker’s character. Shannon’s performance and Horgan’s script are a phenomenal match, outdoing each other at every turn in an endless upward spiral. Whereas in other roles Shannon brilliantly delivers punch lines with gusto, her funniest moments in Divorce are never delivered as jokes but instead with an incredible deadpanned earnestness. After inducing her husband’s heart attack in the pilot by drunkenly wielding and accidentally firing a gun at a party, she is dragged out of her event in handcuffs, telling her guests to help themselves to food. Later, at the hospital, she says, “I don’t want to think about life without him, but if he wakes up, he’s gonna be so mad at me.”

3. Year of the Dog (2007)

Shannon takes center stage in frequent collaborator Mike White’s Year of the Dog, in which she plays Peggy, a lonely woman struck with grief following the unexpected death of her beagle, Pencil. The filmmaking style implemented by White, which heavily features head-on close-ups, proves to be a perfect match for Shannon, highlighting the subtle, minute details of her performance, whether it be the smallest look or furrowed brow. The triumph of the project, and what White and Shannon are able to brilliantly pull off, is that Peggy is never the butt of the joke. Even when she is at her lowest — launching herself out of a closet with a knife to attack the neighbor she holds responsible for Pencil’s death — she’s never pitiful and manages to stand firm as the hero of her own story.

2. Superstar (1999)

Anybody who has ever been to a Blockbuster knows that the only three genres of movies that existed in the ’90s were Meg Ryan rom-com, Titanic, and SNL feature film. Superstar falls in the latter category, giving Shannon’s iconic Mary Katherine Gallagher room to shine in the only SNL movie (out of 11) to be led by a female character (presuming It’s Pat doesn’t count). Of all her iconic characters, Mary Katherine Gallagher gave Shannon the opportunity to flex the most muscle because of the character’s inherently broad range — from the quiet, mousy awkwardness of “Sometimes when I get nervous, I stick my fingers under my arms …,” to the bombastic exclamations of “Superstar!,” to the physicality of launching herself into stacks of folding chairs.

The film, co-starring Ferrell and the iconic Elaine Hendrix as Evian, was unabashedly weird and fully committed to the bit at every turn — whether it was Shannon passionately making out with a tree in front of a nun or Mary Katherine’s parents being killed in a freak Irish-step-dancing accident. But a particular high point is her confession, in which she says, “Father, my sins would best be expressed in a monologue from the made-for-TV movie Sybil, starring a young Miss Sally Field as a woman with multiple-personality disorder,” before launching into said monologue with such fervor that she takes down the confessional booth.

1. Other People (2016)

Shannon delivers a career-best performance in Other People — not just a best for her career but a best for all careers everywhere. Brilliantly written and directed by Chris Kelly, the semi-autobiographical film follows a gay struggling comedy writer who moves home to Sacramento to take care of his mother, Joanne, played by Shannon, as she slowly dies of cancer. It’s a profoundly beautiful but heartbreaking story, teeming with the inherent humor that can exist in the darkest of moments. It’s the finest of lines that only Shannon could walk with such ease, delivering a shattering performance of motherhood and winning her the Film Independent Spirit Award for Best Supporting Actress.

Had Other People rightfully been nominated at the Oscars, the scene that would have played is one in which Joanne sits with her son and husband over milkshakes, making the arrangements for her death. In this scene alone, Shannon demonstrates a fierce protectiveness of the children she is preparing to leave, coming to the brink of tears while also dryly joking about being frozen like a pea and ultimately pulling off her wig in an act of vulnerable defiance. It’s a range of emotion that she doesn’t just flip between but somehow manages to emote simultaneously.

But part of what makes this movie so affecting, and the reason why nobody but Shannon could have pulled it off, is that nobody else is Molly Shannon. After more than 25 years on our screens, audiences have come to know and love the joyful, vibrant performer — so seeing Joanne, a character who shares that same lovable vibrance and humor, slowly slip away hits even harder. There is simply no better showcase of the range and chops that make Shannon an absolute superstar.

Molly Shannon’s Best Roles, Ranked