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Christina Ricci (Young Roberta)
THEN: A 15-year-old Ricci earned one of her first feature film credits for 1995's Now and Then. After making her debut in 1990's Mermaids and rising to fame in The Addams Family, she played a young Roberta Martin in Now and Then. The counterpart to Rosie O'Donnell's adult character, young Roberta was a tomboy who was raised in a family of boys after the death of her mother.
NOW: Now and Then was just the beginning for Ricci, who now has Golden Globe and Emmy nominations to her name. The former child star continued her big-screen career with 1998's The Opposite of Sex, 2003's Monster, and 2008's New York, I Love You. Ricci also picked up television work, making appearances in Malcolm in the Middle, Ally McBeal, and Grey's Anatomy, and starring in ABC's short-lived series Pan Am.
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Rosie O'Donnell (Roberta)
THEN: Sharing the role with Ricci, O'Donnell played the adult version of Roberta Martin. The comedienne became the grown-up tomboy who found a career as a doctor and a steady relationship with a boyfriend. O'Donnell added Now and Then to a filmography that already included A League of Their Own, Sleepless in Seattle, and The Flinstones.
NOW: Soon after Now and Then hit theaters, O'Donnell kicked off a six-year run on The Rosie O'Donnell Show. She also booked gigs in 1996's Harriet the Spy and 1998's Wide Awake, and hit the small screen with roles in Queer as Folk, Nip/Tuck, and The Fosters, in addition to her work co-hosting The View.
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Thora Birch (Young Teeny)
THEN: Just 13 years old at the time of Now and Then's debut, Birch joined the flick after booking late '80s roles in Day by Dayand Doogie Howser, M.D., and 1993's Hocus Pocus. She played the young Tina "Teeny" Tercell, a rich girl with a strong interest in boys, opposite Melanie Griffith.
NOW: Birch continued to act after playing Teeny, picking up one-off gigs in CBS' 1990s series Promised Land, a 1997 episode of Touched by an Angel, and Fox's 2001 project Night Visions. The Los Angeles native also appeared in 2000's Dungeons & Dragons, the 2003 Lifetime movie Homeless to Harvard: The Liz Murray Story, and recently booked a starring role in the upcoming USA series Colony.
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Melanie Griffith (Teeny)
THEN: Already a household name when Now and Then hit theaters, Griffith played the grown-up Teeny, a glamorous Hollywood actress. The project came to the star 20 years after she made her big-screen debut, following films including 1984's Body Double, 1988's Working Girl, and 1992's Shining Through.
NOW: Griffith was busy as ever after Now and Then, continuing her career with parts in 1996's Mulholland Falls, 1997's Lolita, and 2000's Cecil B. DeMented. In recent years, she's appeared in 2012 episodes of Raising Hope, had a 2014 turn on Hawaii Five-0, and dropped in on an episode of Saturday Night Live, hosted by her Fifty Shades of Grey-starring daughter Dakota Johnson.
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Gaby Hoffman (Young Samantha)
THEN: The Field of Dreams star joined Now and Then as the young Samantha Albertson. The 13-year-old Hoffman played the eccentric girl with a passion for the supernatural after earning previous credits for 1989's Uncle Buck, 1992's This Is My Life, and 1993's Sleepless in Seattle.
NOW: Hoffman appeared in 1997's Volcano, 1998's All I Wanna Do, and 2000's You Can Count on Me before taking a bit of a break from acting in the early 2000s. Her career picked back up in recent years with celebrated turns as Ali in Amazon's Transparent and Caroline in HBO's Girls, as well roles in the offbeat 2014 comedy Obvious Child and the Oscar-nominated Wild.
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Demi Moore (Samantha)
THEN: Moore starred opposite Hoffman as the adult Samantha. The narrator of the film, Samantha grows up to become an author. Moore took on the role after previous appearances in 1985's St. Elmo's Fire, 1986's About Last Night…, 1990's Ghost, 1992's A Few Good Men, and 1993's Indecent Proposal.
NOW: The star added dozens of lines to her filmography following Now and Then. She hit the big screen in 1996's Striptease, 1997's G.I. Jane, 2003's Charlie's Angels: Full Throttle, and 2011's Margin Call. Moore also made headlines for her personal life with a 1990s marriage to Bruce Willis and a late 2000s relationship with Ashton Kutcher.
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Ashleigh Aston Moore (Young Chrissy)
THEN: Moore found her place in Now and Then after starring in the Candian series The Odyssey and making a 1995 cameo on CBS' Northern Exposure. The child star played young Chrissy DeWitt, a well-behaved little girl who kept her friends in line.
NOW: Moore continued to act for just two years after Now and Then, appearing in the 1996 movie The Grave, and making cameos in Fox's Strange Luck and the TV movie A Friend's Betrayal. Moore's last listed credit was for a 1997 episode of Touched by an Angel, 10 years before her reported death at the age of 26 in December 2007.
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Rita Wilson (Chrissy)
THEN: Wilson played the pregnant, married, adult counterpart to Moore's Chrissy. Before booking the gig, Wilson made TV appearances in The Brady Bunch, Hawaii Five-0, M*A*S*H, and Happy Days in the 1970s and 1980s. She went on to nab a role in 1989's Teen Witch, and star opposite husband Tom Hanks in 1993's Sleepless in Seattle.
NOW: Following Now and Then, Wilson reunited onscreen with Hanks in 1996's That Thing You Do!, and appeared in 1998's Psycho, 1999's Runaway Bride, 2009's Old Dogs, and 2011's Larry Crowne. Wilson also expanded her work to the small screen with The Good Wife, Girls, and Full Circle, and to the stage with the Broadway revival of Chicago and 2015's Fish in the Dark.
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Devon Sawa (Scott Wormer)
THEN: '90s favorite Sawa joined the cast of Now and Then as neighborhood boy and eventual Roberta-kisser, Scott Wormer. The child star appeared alongside Moore in The Odyssey, booking roles in 1994's Little Giants and 1995's Casper soon after.
NOW: Sawa continued his busy decade with parts in 1997's Wild America, 1998's A Cool, Dry Place, 1999's Idle Hands, and a turn in the 1990s animated series Action Man. Sawa went on to star in the first Final Destination movie in 2000, made a cameo in a 2010 episode of NCIS: Los Angeles, and spent three years on Nikita as Sam Matthews.
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Cloris Leachman (Grandma Albertson)
THEN: Veteran actress Leachman played Grandma Albertson to Hoffman's Samantha in Now and Then. She picked up the role as the maternal figure well into her career, having already been in the business for more than 50 years. Leachman's pre-Now and Then projects include her turn as Phyllis in the 1970s' Mary Tyler Moore and Phyllis, and the two years she spent playing Beverly Ann Stickle on The Facts of Life.
NOW: Leachman continues to act well into her eighties. Turning 90 in 2016, the beloved actress followed up Now and Then with an early 2000s turn on The Ellen Show, an appearance in 2003's Bad Santa, a recent role as Maw Maw in Raising Hope, and parts in 2008's The Women, 2010's You Again, and 2015's The Wedding Ringer.
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Janeane Garofalo (Wiladene)
THEN: Garofalo had a brief but memorable role in Now and Then as the dubious psychic Wiladene. She came into the part after booking a gig as a Saturday Night Live cast member and making appearances in The Ben Stiller Show and 1994's Reality Bites.
NOW: After Now and Then's debut, Garofalo starred in 1997's Romy and Michele's High School Reunion, 1999's Dogma, and 2001's Wet Hot American Summer. In recent years, the star appeared as Beth Griffith in Criminal Minds: Suspect Behavior, joined Girlfriends' Guide to Divorce as Lyla, and signed on for Netflix's Wet Hot American Summer reboot.
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Hank Azaria (Bud Kent)
THEN: Azaria played Now and Then's Bud Kent, a potential suitor to Samantha's mother. One of the actor's earlier resume lines, the role came to Azaria after he spent four years on the 1990s Fox series Herman's Head, appeared in 1994's Quiz Show opposite Ralph Fiennes and Rob Morrow, and played Craig on CBS' If Not for You.
NOW: The actor's schedule picked up after the movie, with big-screen turns in 1998's Great Expectations, 2004's Dodgeball: A True Underdog Story, and 2009's Night at the Museum: Battle of the Smithsonian. Azaria also hit television as David in Friends, held various voice roles in The Simpsons, and played Ed in Ray Donovan.
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Bonnie Hunt (Mrs. DeWitt)
THEN: After appearing in NBC's Grand in 1990, the short-lived early '90s series Davis Rules, and two Beethoven movies, Hunt joined Now and Then as Mrs. DeWitt, the strict mother to Moore's Chrissy DeWitt.
NOW: The following year, Hunt starred in 1996's Jerry Maguire, going on to lend her voice to 2001's Monsters, Inc. and 2006's Cars, and star in ABC's early 2000s series Life With Bonnie. Hunt recently returned to her voice role in 2013's Monsters University, and is expected to once again voice Dolly in the upcoming Toy Story 4.