PHOTOS: ‘Sleepless in Seattle’ Cast Then & Now

Is there a movie as iconic as “Sleepless in Seattle”? The 1993 romantic classic also helped cement Tom Hanks and Meg Ryan as two of the most reliable romantic leads of their era, setting the stage for their later reunion in “You’ve Got Mail.”

Released in 1993 and directed by Nora Ephron, the film centers on widowed father Sam Baldwin and his young son Jonah as they attempt to rebuild their lives after moving to Seattle.

Still mourning the loss of his mother, Jonah calls into a late-night radio show in hopes of finding his father’s love again. Listeners across the country are drawn to Sam’s vulnerability, including reporter Annie Reed. Though engaged, Annie feels an unexpected connection and writes Sam a letter asking him to meet her atop the Empire State Building in New York City on Valentine’s Day.

Getty

She ultimately leaves dinner with her fiancé and heads to the rooftop, where Jonah and Sam are waiting.

The final scene, inspired by “An Affair to Remember,” has since become one of the most iconic moments in romantic-comedy history. The film treats Sam’s grief with care, captures Jonah’s hopeful determination, and follows Annie’s longing for something more than her predictable life in Baltimore.

Curious where Sam, Annie, and the rest of the cast ended up? Here’s what the stars of “Sleepless in Seattle” have been doing since 1993.

1. Tom Hanks: From Sam Baldwin to Hollywood Icon

Getty

The Oscar-winning actor starred as widower Sam Baldwin, a performance that further established Tom Hanks as one of Hollywood’s most dependable leading men.

In the years following “Sleepless in Seattle,” he anchored an extraordinary run of films, including “Forrest Gump,” “Apollo 13,” “You’ve Got Mail,” “Cast Away,” “Bridge of Spies,” “Sully,” “A Beautiful Day in the Neighborhood,” and “News of the World.”

He also became the voice of Woody in the “Toy Story” franchise beginning in 1995, a role he continues to reprise.

Beyond acting, Hanks built a prolific career behind the scenes, narrating the HBO miniseries “The Pacific” and amassing more than 50 producer credits across film and television, including “Big Love,” “The Sixties,” “The Movies,” “Mamma Mia! Here We Go Again,” and “In the Garden of Beasts.”

Although he had already gained recognition through projects such as “Bosom Buddies,” “Big,” and “A League of Their Own,” Hanks’ career reached new heights shortly after “Sleepless in Seattle,” when he won back-to-back Academy Awards for Best Actor for “Philadelphia” and “Forrest Gump.”

He has since earned seven Emmys, four Golden Globes, including the Cecil B. DeMille Award, and two SAG Awards, among numerous other honors.

Getty Images

Offscreen, Hanks was married to Samantha Lewes from 1978 to 1987 and shares two children with her, Colin Hanks and Elizabeth Hanks.

He has been married to Rita Wilson, who also appeared in “Sleepless in Seattle,” since 1988, and the couple shares two sons, Chet Hanks and Truman Hanks.

2. Meg Ryan: The Rom-Com Star Who Defined an Era

Getty

Ryan portrayed reporter Annie Reed, whose unexpected connection to Sam begins after hearing him and his young son on a late-night radio show. By the time she took on the role, Ryan was already establishing herself as one of the defining romantic leads of the late 1980s and early 1990s, following breakout performances in “When Harry Met Sally” and “Joe Versus the Volcano,” the latter of which also paired her opposite Hanks.

Getty

After “Sleepless in Seattle,” Ryan continued her run in romantic dramas and comedies, starring in films such as “When a Man Loves a Woman,” “City of Angels,” “You’ve Got Mail,” “Kate & Leopold,” and “In the Land of Women.”

She later expanded her career behind the camera, directing and starring in “Ithaca” and returning to the screen with “What Happens Later.”

Ryan also voiced the title character in the animated film “Anastasia” and began producing films in the mid-1990s, with credits including “The Wedding Planner,” “Desert Saints,” and “Picture Paris.”

Ryan has earned three Golden Globe nominations, including one for “Sleepless in Seattle.”

Offscreen, she was married to actor Dennis Quaid from 1991 to 2001, and they share a son, Jack Quaid. She adopted her daughter, Daisy True, in 2006. Ryan was later in an on-and-off relationship with musician John Mellencamp, with the couple calling off their engagement in 2019.

Ross Malinger: The Heart of Jonah Baldwin

Malinger played Jonah Baldwin, Sam’s thoughtful and big-hearted son whose late-night radio call sets the film’s love story in motion.

Just 8 years old when “Sleepless in Seattle” was released, Malinger stood out as a gifted child actor, earning attention for a performance defined by sincerity and emotional awareness well beyond his age.

Following the film’s success, Malinger continued acting through the 1990s and early 2000s. His television credits include “Good Advice,” “Nick Freno: Licensed Teacher,” “Party of Five,” “Touched by an Angel,” and “Seinfeld.” He also voiced Theodore J. “T.J.” Detweiler on the animated series “Recess,” becoming a familiar presence in family-friendly television of the era.

Malinger stepped away from acting after appearing in a 2006 episode of “Without a Trace” and has largely remained out of the public spotlight since.

Bill Pullman: Annie Reed’s Fiancé and a Versatile Career

Getty

Pullman played Walter, Annie Reed’s reliable but unexciting fiancé, whose presence quietly highlights her growing sense that something is missing.

Though his role in “Sleepless in Seattle” was a supporting one, Pullman’s subtle performance helped ground the film’s emotional tension.

After the film, Pullman built a versatile career across movies, television, and theater. His film credits include “Wyatt Earp,” “Casper,” “Independence Day,” “Battle of the Sexes,” and “Dark Waters.” On television, he appeared in series such as “Torchwood,” “1600 Penn,” and the acclaimed drama “The Sinner.”

He also made his directing debut with “The Virginian” and has continued working on stage, including in productions such as “All My Sons.”

Pullman has been married to dancer Tamara Hurwitz since 1987, and the couple shares three children.

Rosie O’Donnell: Annie’s Best Friend and a Comedy Powerhouse

Getty

O’Donnell played Becky, Annie Reed’s quick-witted best friend and trusted confidante, bringing humor and heart to the film’s quieter moments. Her performance helped balance the romance with grounded friendship. After “Sleepless in Seattle,” O’Donnell built a diverse career across film, television, and comedy.

She appeared in movies including “Now and Then,” “Harriet the Spy,” and “Tarzan.” At the same time, her television work includes roles on “The Fosters,” “SMILF,” “I Know This Much Is True,” and “The L Word: Generation Q.”

She later returned to familiar territory with a role in the “A League of Their Own” television series, decades after playing Doris Murphy in the 1992 film. O’Donnell also hosted “The Rosie O’Donnell Show” for seven seasons and went on to produce projects such as “The Big Gay Sketch Show” and “The Specials.”

She served as a cohost on “The View” from 2006 to 2007 and again from 2014 to 2015.

Away from the screen, O’Donnell is a mother of five. She adopted her son, Parker, in 1995, and later adopted Chelsea and Blake with her former partner, Kelli Carpenter. She welcomed her daughter, Vivienne, via artificial insemination.

O’Donnell married Michelle Rounds in 2012, and the pair adopted a daughter, Dakota, before separating in 2014. She later dated Aimee Hauer, whose relationship ended in 2022.

Rita Wilson: From Suzy to a Multifaceted Hollywood Career

Getty

Wilson portrayed Suzy, Sam Baldwin’s steady and compassionate sister, bringing warmth and grounding to the film’s emotional world.

After “Sleepless in Seattle,” she carved out a versatile career across film, television, theater, and music.

Her screen credits include “Jingle All the Way,” “Now and Then,” “Runaway Bride,” “Gloria Bell,” “A Simple Wedding,” and “Boy Genius,” along with television appearances on series such as “The Good Wife,” “Full Circle,” and Lena Dunham’s iconic HBO series—“Girls.”

Behind the scenes, Wilson has made a lasting impact as a producer. Her work includes the “My Big Fat Greek Wedding” franchise, the “Mamma Mia!” films, and “A Man Called Ove.” She also returned to the stage in a major way, stepping into the role of Roxie Hart during the 2006 Broadway run of “Chicago.”

In music, Wilson launched a solo career with her debut album, “AM/FM,” in 2012 and has since released three additional records.

Offscreen, Wilson has been married to Tom Hanks since 1988. The couple shares two sons, Truman and Chet, and she is also stepmother to Colin and Elizabeth, whom Hanks shares with his late former wife, Samantha Lewes. A breast cancer survivor, Wilson was declared cancer-free in 2015.

Victor Garber: From ‘Sleepless in Seattle’ to Acclaimed TV & Broadway Career

Getty

Garber portrayed Greg, Suzy’s husband, offering a calm and supportive presence in “Sleepless in Seattle.” Following the film, he built an acclaimed career across television, film, and theater, becoming one of the most recognizable character actors of his generation.

On television, Garber found major success with roles on series including “Alias,” “Justice,” “Eli Stone,” “Deception,” “Web Therapy,” “The Flash,” “The Orville,” “Power,” “DC’s Legends of Tomorrow,” and “Family Law,” which premiered in 2021. His film work spans titles such as “The First Wives Club,” “Titanic,” “Legally Blonde,” “Argo,” and “Happiest Season.”

He was recently seen in “And Just Like That”— the sequel to the hit HBO series “Sex & the City”.

A classically trained performer, Garber has also maintained a strong presence on stage. His Broadway credits include “Damn Yankees,” “Arcadia,” “Present Laughter,” and “Hello, Dolly!” The Canadian-born actor married artist Rainer Andreesen in 2015 after five years together.

Rob Reiner: Beloved Actor, Legendary Director & Lasting Hollywood Legacy

Getty

Reiner played Jay, Sam Baldwin’s close friend and dating adviser, bringing humor and perspective to “Sleepless in Seattle.”

Long before the film, Reiner became a household name as Mike Stivic on the groundbreaking Norman Lear sitcom “All in the Family,” a role that launched his career in television and film.

Behind the camera, Reiner emerged as one of Hollywood’s most influential directors. His work includes “This Is Spinal Tap,” “Stand by Me,” “The Princess Bride,” “When Harry Met Sally…,” “Misery” and “A Few Good Men,” films that helped define modern American storytelling.

He also appeared in projects such as “The Story of Us,” “The Wolf of Wall Street,” “Shock and Aw,e” and television’s “New Girl.” In addition, Reiner accumulated more than 50 writing credits, including work on the 2001 and 2013 Emmy Awards and the 2017 Kennedy Center Honors.

Born in the Bronx in 1947, Reiner was the son of comedy legend Carl Reiner and actress and singer Estelle Lebost. He was married to Penny Marshall from 1971 to 1981 and adopted her daughter, Tracy Reiner. He later married photographer Michele Singer in 1989, whom he met while directing “When Harry Met Sally….” The couple shared three children, Jake, Nick, and Romy.

The BBC reported that Reiner and Singer were found dead in their Los Angeles home on December 14. Their son Nick has since been charged with two counts of first-degree murder in connection with their deaths, a tragedy that sent shockwaves through Hollywood and marked a devastating end to the life of an iconic filmmaker and a complete family man.

The post PHOTOS: ‘Sleepless in Seattle’ Cast Then & Now appeared first on EntertainmentNow.