1. Molly Ringwald
Written by the legendary John Hughes and released on February 28, 1986, Pretty in Pink became an instant classic, capturing the hearts of a generation. Molly Ringwald was only 18 years old when she played the resilient Andie Walsh in 1986. Having already starred in Sixteen Candles in 1984 and The Breakfast Club in 1985, she was the ultimate face of the “Brat Pack” era. However, as the 1990s approached, Molly made the brave choice to move to France to seek a more private life and explore independent film projects. This period of reflection allowed her to transition from a teen idol into a versatile actress, eventually returning to the U.S. for steady work in hits like The Secret Life of the American Teenager and the popular CW series Riverdale.
In recent years, Molly has flourished as a writer and jazz singer, releasing her debut album, Except Sometimes, in 2013. She has also gained respect as a thoughtful cultural critic, writing poignant essays for The New Yorker that re-examine her early films through a modern lens. Now a mother of three, she balances her time between acting and her literary pursuits. Ringwald’s journey is a masterclass in how to outgrow a famous persona while still honoring the work that started it all. She remains a beloved icon who has successfully defined herself on her own terms.
2. Jon Cryer
Jon Cryer stole the show as the quirky, devoted Duckie Dale, a character that earned him a permanent spot in pop culture history. Despite the film’s success, Cryer spent much of the late 1980s and 1990s trying to find a role that didn’t feel like a shadow of Duckie. He worked steadily in various films and short-lived sitcoms, but his big “second act” didn’t arrive until 2003. That was the year he was cast as the neurotic Alan Harper on the massive hit Two and a Half Men, a role he played for twelve highly successful seasons until 2015.
His performance on the sitcom was legendary, making him the only actor to win Primetime Emmy Awards for both Supporting Actor and Lead Actor for the same show. In 2015, he released a candid memoir titled So That Happened, where he shared the ups and downs of his long career with self-deprecating humor. More recently, he joined the DC Universe as the villainous Lex Luthor in the Supergirl series, proving his range goes far beyond comedy. Today, Jon is celebrated for his resilience and is often seen engaging with fans who still feel a deep connection to the “Duckman” decades later.
3. Andrew McCarthy
Andrew McCarthy played Blane McDonough, the wealthy “preppy” with a heart of gold who eventually won Andie’s heart. Following the film’s 1986 release, he became a major star in hits like Mannequin and Weekend at Bernie’s. However, by the early 1990s, McCarthy began to feel disillusioned with the pressures of being a Hollywood heartthrob. He decided to pivot, finding a new passion in travel writing and directing. His transition was remarkably successful, as he became a contributing editor for National Geographic Traveler and an award-winning author of books like The Longest Way Home.
Behind the camera, Andrew has built an impressive resume directing episodes of high-profile shows such as Orange Is the New Black and The Blacklist. In 2021, he released Brat: An 80s Story, a memoir that explored his complicated relationship with fame during his youth. Most recently, in 2024, he directed the documentary Brats, which reunited him with several former co-stars to discuss their shared legacy. Today, Andrew is widely respected for his intellect and creative honesty. He has successfully traded the flashing lights of the red carpet for the quiet fulfillment of storytelling, proving that there is plenty of life after being a teenage pin-up.
4. Annie Potts
Annie Potts provided the film’s emotional backbone as Iona, the quirky record store owner who served as a mentor to Andie. By the time Pretty in Pink hit theaters, Potts was already a familiar face thanks to her role in the 1984 blockbuster Ghostbusters. She continued her winning streak on television, starring in the beloved sitcom Designing Women from 1986 to 1993. Perhaps her most enduring contribution to cinema, however, began in 1995 when she voiced the character of Bo Peep in Disney’s Toy Story, a role she reprised to great acclaim in 2019’s Toy Story 4.
In more recent years, Annie has reached a whole new audience playing the feisty “Meemaw” on the hit series Young Sheldon, which premiered in 2017. Her performance as the gambling, wise-cracking grandmother became a fan favorite over its seven-season run. Off-screen, she is a dedicated mother and an advocate for various charitable causes. Annie has often spoken about the joy of being a working actress in her 70s, emphasizing that she values interesting characters over vanity. Her career is a shining example of longevity in Hollywood, built on a foundation of genuine talent, a sharp sense of humor, and an incredible ability to adapt.
5. James Spader
James Spader was perfectly cast as the arrogant and wealthy Steff, the villain audiences loved to hate in 1986. While many of his peers stayed in the “teen movie” lane, Spader immediately began seeking out darker, more provocative roles. This led to his breakout performance in the 1989 independent film Sex, Lies, and Videotape, which won him the Best Actor award at the Cannes Film Festival. Throughout the 1990s, he became known for his intense and often eccentric characters in films like Stargate and the controversial but acclaimed drama Crash.
In the 2000s, Spader made a massive impact on television, winning three Emmy Awards for his portrayal of the brilliant lawyer Alan Shore on The Practice and its spin-off Boston Legal. He followed this success with a decade-long run as the criminal mastermind Raymond “Red” Reddington on The Blacklist, which concluded in 2023. Spader has always maintained a high level of privacy regarding his personal life, rarely giving interviews or appearing on social media. Today, he is regarded as one of the most compelling actors of his generation. His journey from a “Brat Pack” antagonist to a heavyweight of dramatic television shows just how much depth he brought to the industry.
6. Harry Dean Stanton
Harry Dean Stanton played Andie’s father, Jack Walsh, bringing a sense of warmth and vulnerability to the film. When he joined the cast in 1986, Stanton was already a legendary character actor with a career dating back to the 1950s. He was a favorite of directors like David Lynch and had starred in masterpieces such as Paris, Texas in 1984. Following Pretty in Pink, he continued to work tirelessly, appearing in everything from The Green Mile to the 2017 revival of Twin Peaks. His presence on screen always added a layer of soulful authenticity.
Stanton passed away peacefully in September 2017 at the age of 91, leaving behind an incredible body of work. His final starring role was in the film Lucky, released the same year he died, which served as a beautiful and poignant tribute to his life and philosophy. Harry Dean was also an accomplished musician who frequently performed with his own band. He never cared for the glitz of Hollywood, preferring to focus on the truth of the human experience. His legacy in Pretty in Pink remains one of the most touching portrayals of fatherhood in 80s cinema. He will always be remembered as an actor who could say more with a single look than most could with a page of dialogue.
7. Kate Vernon
Kate Vernon played Benny Hanson, the popular girl who often clashed with Andie’s social circle. Although her role in the 1986 film was a supporting one, it served as a solid stepping stone for a long and productive career. Throughout the late 1980s and 1990s, Kate became a fixture on television, appearing in popular shows like Who’s the Boss? and Murder, She Wrote. She also landed a significant recurring role on the hit series Nash Bridges alongside Don Johnson. Her ability to play complex, strong-willed women quickly made her a favorite among casting directors.
Vernon’s career reached a new peak in 2004 when she was cast as the mysterious Ellen Tigh in the critically acclaimed reimagining of Battlestar Galactica. The role earned her a dedicated following in the science fiction community and allowed her to showcase her dramatic range. In more recent years, she has appeared in shows like The 100 and the hit Marvel series The Punisher. Now in her 60s, Kate continues to work steadily in both film and television. While she may not be the most famous face from the Pretty in Pink poster, her career is a testament to the endurance and skill required to remain a working actress in Hollywood for forty years.
8. Andrew Dice Clay
Andrew Dice Clay had a very brief, “blink-and-you’ll-miss-it” appearance as a bouncer at the club in Pretty in Pink. At the time, he was a struggling actor and comedian looking for his big break. That break came just a few years later in the late 1980s when his “Dice” persona exploded in popularity. He became the first comedian to sell out Madison Square Garden for two consecutive nights in 1990. While his abrasive and controversial stand-up style made him a household name, it also led to a significant amount of professional backlash and a decline in his mainstream career by the mid-90s.
However, the 21st century brought a surprising and well-deserved career resurgence for Clay. He moved away from his stage persona and began taking on serious dramatic roles that shocked critics with their depth. He received rave reviews for his performance in Woody Allen’s Blue Jasmine in 2013 and played Lady Gaga’s father in the 2018 smash hit A Star Is Born. These roles proved that underneath the leather jacket and tough-guy act was a truly talented actor. Today, Andrew continues to perform stand-up while enjoying a newfound respect in the film industry. His journey from a movie bouncer to a respected dramatic actor is one of Hollywood’s most interesting turnaround stories.
9. Gina Gershon
Gina Gershon appeared briefly in Pretty in Pink as a high school student, long before she became a celebrated star in her own right. Her career truly caught fire in the 1990s when she took on bold, boundary-pushing roles that defined the decade. She starred in the 1995 cult classic Showgirls and the 1996 neo-noir thriller Bound, which established her as a fearless actress willing to take risks. These performances made her an icon of independent cinema and showed that she was much more than just a supporting player.
Beyond her work in film, Gina has had a flourishing career on Broadway, appearing in productions like Cabaret and Bye Bye Birdie. She is also an accomplished author, having written children’s books and a memoir about her search for her feline companion. More recently, she joined the cast of Riverdale, playing the mother of Jughead Jones, which brought her back to the world of teen drama with a mature twist. Today, Gina is known for her cool, sophisticated screen presence and her refusal to be typecast. Her small start in a 1986 teen movie was just the beginning of a rich, multi-faceted career that spans acting, music, and writing.
10. Kristy Swanson
Kristy Swanson had a small, uncredited role as a student in Pretty in Pink, marking one of her very first professional appearances. It wasn’t long before she transitioned into leading roles, most notably starring as the original Buffy in the 1992 film Buffy the Vampire Slayer. Throughout the early 1990s, she was a constant presence on the big screen, appearing in films like The Program, The Chase, and the cult classic Higher Learning. Her blonde hair and athletic build made her the quintessential girl-next-door for the 90s generation.
As she moved into the 2000s, Swanson’s career shifted more toward television movies and guest appearances on shows like Psych and Seal Team. She also ventured into reality television, winning the competition show Skating with Celebrities in 2006. While her path has been more varied and sometimes quieter than her Pretty in Pink co-stars, she remains a recognizable figure to anyone who grew up with 90s cinema. Today, Kristy continues to act in independent projects and enjoys attending fan conventions where she meets those who remember her early days. Her career serves as a reminder that even the smallest background roles can lead to a lifetime of opportunities in the entertainment world.
11. Alexa Kenin
Alexa Kenin played the role of Jena Hoeman, Andie’s supportive and down-to-earth friend at school. Kenin was a rising talent in the 1980s, having previously appeared in films like Little Darlings (1980) and alongside Clint Eastwood in Honkytonk Man (1982). She brought a natural, relatable energy to her scenes, serving as a grounded contrast to the high-fashion drama of the main plot. Tragically, the world never got to see her full potential. On September 10, 1985, just months before Pretty in Pink was released in theaters, Alexa was found dead in her Manhattan apartment at the young age of 23.
The film was dedicated to her memory upon its release in February 1986. While the circumstances of her passing remained a private family matter, her colleagues often spoke of her professionalism and vibrant spirit on set. Today, Alexa’s performance remains a poignant part of the movie’s history, representing the many young dreams that define the 1980s era. Fans still revisit her work, noting how she held her own among a cast of future superstars. Though her life was cut short, her contribution to this iconic film ensures she remains a permanent part of the “Brat Pack” cinematic legacy for new generations of viewers to discover.
12. Dweezil Zappa
Dweezil Zappa made a memorable cameo as Simon, the quirky guy with the tall hair at the prom who attempts to talk to Andie. The son of legendary musician Frank Zappa, Dweezil was only 16 years old when the film was released in 1986. While he explored acting during this period, appearing in films like The Running Man in 1987, his true calling was always the guitar. He spent much of the 1990s and early 2000s releasing solo albums and working as a VJ for MTV, where his musical knowledge and laid-back personality made him a favorite among fans of the network’s rock programming.
In 2006, Dweezil launched “Zappa Plays Zappa,” a massive touring project dedicated to performing his father’s complex musical compositions for a modern audience. The project was a huge success, winning a Grammy Award in 2009 for Best Rock Instrumental Performance. He has also become a highly respected guitar instructor, sharing his technical mastery through online masterclasses and clinics. Today, Dweezil continues to tour and record, maintaining a deep connection to his family’s artistic heritage while carving out his own path as a virtuoso. His brief appearance in Pretty in Pink remains a fun trivia fact for fans, marking a moment before he became a pillar of the global guitar community.
13. Margaret Colin
Margaret Colin appeared in Pretty in Pink as the English teacher who tries to keep order in the classroom. While her role was small, Colin’s career was already on an upward trajectory. She moved from the classroom of a teen movie to the high-stakes world of 80s blockbusters, starring in Three Men and a Baby in 1987. Throughout the 1990s, she became a very familiar face to moviegoers, most notably playing Constance Spano, the White House Communications Director, in the 1996 sci-fi smash hit Independence Day. Her ability to project intelligence and authority made her a go-to actress for sophisticated professional roles.
In the 2000s, Margaret found a whole new level of fame on television. From 2007 to 2012, she played Eleanor Waldorf, the fashion-designer mother of Blair Waldorf, on the massive hit Gossip Girl. This role brought her career full circle, returning her to the world of high-school social hierarchies and elite drama. More recently, she has appeared on shows like Veep and Chicago Med, proving her talent is as sharp as ever. Today, Margaret continues to work in film and theater, balancing her professional life with her longtime marriage to actor Justin Deas. Her journey from a background teacher in 1986 to a cornerstone of modern television drama is a testament to her incredible range and staying power.
14. Jim Haynie
Jim Haynie played Mr. Donnelly, the authoritative yet fair high school principal who had the difficult task of managing the “richies” and the outsiders alike. Following the film’s release in 1986, Haynie continued to build a prolific career as a dependable character actor. He appeared in dozens of popular television shows and films throughout the 80s and 90s, including The Bridges of Madison County (1995) and the action hit The Peacemaker (1997). His weathered, fatherly presence made him a natural fit for roles in Westerns, dramas, and police procedurals, where he often played figures of quiet strength or wisdom.
Haynie remained active in the industry well into his 70s, with later roles in shows like Justified and American Horror Story. He was also deeply involved in the San Francisco theater scene, where he was respected for his commitment to the craft of stage acting. Sadly, Jim Haynie passed away in April 2021 at the age of 81 due to complications from Alzheimer’s disease. He is remembered by his colleagues as a “gentle giant” of the acting world who brought dignity to every role, no matter how small. In Pretty in Pink, he provided a necessary adult anchor to the teenage chaos, a role he played with a subtlety that helped ground the film’s more heightened emotional moments.
15. Maggie Roswell
Maggie Roswell had a brief but memorable role in the film as a “dietician” in the high school cafeteria scene. While her face might not be instantly recognizable to everyone, her voice certainly is. Shortly after Pretty in Pink, Roswell joined the cast of a fledgling animated show called The Simpsons in 1990. She became the voice of several iconic characters, most notably the virtuous Maude Flanders, the eccentric Miss Hoover, and the wealthy Luann Van Houten. Her work on the show has spanned over three decades, making her a vital part of one of the most successful franchises in television history.
In addition to her work in Springfield, Maggie has provided voices for numerous other animated projects and has appeared in guest roles on live-action shows like Murphy Brown. She also spent many years performing in regional theater and running a recording studio with her husband. Today, Maggie continues to be a key member of the Simpsons voice cast, returning to her roles even after a brief hiatus in the late 90s due to a contract dispute. Her career is a fascinating example of how a small, live-action part in an 80s movie can lead to a legendary career behind the microphone. She remains a beloved figure in the world of voice acting, bringing humor and heart to characters that have become global icons.
16. Christian Jacobs
Christian Jacobs was just a child when he appeared in Pretty in Pink as a kid in the record store. While he continued to act in commercials and small TV roles throughout the late 80s, his true passion lay in music and creative production. In the early 1990s, he co-founded the band The Aquabats, a theatrical rock group known for their superhero costumes and high-energy performances. Jacobs, performing under the stage name “The MC Bat Commander,” led the band to cult status and helped launch the career of their one-time drummer, Travis Barker.
Jacobs’ greatest professional success came in 2007 when he co-created the hit children’s television series Yo Gabba Gabba!. The show became a global phenomenon, praised for its music, celebrity guests, and positive messages. It earned several Emmy nominations and turned Jacobs into a major force in children’s entertainment. More recently, he has continued to produce new content for various networks while still touring with The Aquabats. Today, Christian is recognized as a visionary creator who successfully bridged the gap between indie rock and family-friendly media. His tiny role in a 1986 record store now feels like a prophetic moment for a man who would spend his life surrounded by music and pop culture.
17. Emily Longstreth
Emily Longstreth played Kate, one of the popular girls who orbited around James Spader’s character, Steff. Following Pretty in Pink in 1986, Emily appeared to be on the verge of a major career, starring in the 1987 teen comedy Can’t Buy Me Love alongside Patrick Dempsey. She also landed roles in various television movies and guest spots on popular shows like Growing Pains. Her classic 80s look and natural charm made her a frequent choice for the “popular girl” archetype that defined the era’s cinema.
By the mid-1990s, however, Emily made the personal decision to step away from the Hollywood spotlight. She transitioned into a more private life, moving away from acting to focus on other interests and her family. Unlike many of her co-stars who sought lifelong fame, Emily’s path reflects a common Hollywood story of someone who enjoyed a period of success before choosing a different, quieter road. Today, she remains a nostalgic figure for fans of 80s teen cinema. While she is no longer active in the industry, her performances in two of the decade’s most iconic films ensure her place in pop culture history. Her journey serves as a reminder that success doesn’t always have to be measured by decades of visibility, but can also be found in the quality of a few memorable moments.
18. Jamie Anders
Jamie Anders appeared in the film as a student, contributing to the lived-in, authentic feel of the high school environment that John Hughes was famous for creating. Like many young actors in the mid-80s, Anders worked steadily in small roles across various television series, including The Facts of Life and St. Elsewhere. These early experiences provided a front-row seat to the golden age of 80s television production. However, as the decade came to a close, Jamie found that his interests were shifting away from performing and toward the technical and business sides of the entertainment industry.
In the years following his time on the Pretty in Pink set, Jamie transitioned into production and talent management. He found a niche helping other artists navigate their careers, using his early experience as a child actor to provide valuable insight into the pressures of the industry. Today, Jamie maintains a much more private profile than his famous co-stars. His career path is representative of many “background” stars who used their early exposure to film sets as a foundation for successful, long-term careers behind the scenes. While he may not be signing autographs at conventions, his work has helped support the infrastructure of the entertainment world for decades, proving there are many ways to build a life in Hollywood.
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