Here's what Elaine Hendrix looked like as Meredith Blake in The Parent Trap (1998): Disney / Courtesy of Everett Collection
Here's what Elaine Hendrix looks like today: Here's what Omar Epps looked like as Quincy McCall in Love & Basketball (2000): New Line Cinema / Courtesy of Everett Collection
Here's what Omar Epps looks like today: Jamie Mccarthy / Getty Images for STARZ
Here's what Rupert Everett looked like as George Downes in My Best Friend's Wedding (1997): Sony Pictures Releasing / Courtesy of Everett Collection
Here's what Rupert Everett looks like today: Laurent Viteur / Getty Images
Here's what Larisa Oleynik looked like as Bianca Stratford in 10 Things I Hate About You (1999): Buena Vista Pictures / Buena Vista Pictures/Courtesy of Everett Collection
Here's what Larisa Oleynik looks like today: Tibrina Hobson / Getty Images
Here's what Lela Rochon looked like as Robin Stokes in Waiting to Exhale (1995): 20th Century Fox / Courtesy of Everett Collection
Here's what Lela Rochon looks like today: Leon Bennett / FilmMagic / Getty Images
Here's what Kathryn Hahn looked like as Michelle in How to Lose a Guy in 10 Days (2003): Paramount Pictures / Courtesy of Everett Collection
Here's what Kathryn Hahn looks like today: Todd Williamson / NBCU Photo Bank via Getty Images
Here's what Donald Faison looked like as Murray Duvall in Clueless (1995): Paramount Pictures / Courtesy of Everett Collection
Here's what Donald Faison looks like today: Eric Liebowitz / ABC via Getty Images
Here's what Sanaa Lathan looked like as Sid Shaw in Brown Sugar (2002): 20th Century Fox / Courtesy of Everett Collection
Here's what Sanaa Lathan looks like today: Arnold Turner / Getty Images for Freedom Road Productions
Here's what Annie Potts looked like as Iona in Pretty in Pink (1986): Paramount Pictures / Courtesy of Everett Collection
Here's what Annie Potts looks like today: Rich Polk / Getty Images
Here's what Anthony Michael Hall looked like as Ted Farmer in Sixteen Candles (1984): MCA / Courtesy of Everett Collection
Here's what Anthony Michael Hall looks like today: Valerie Macon / AFP via Getty Images
Here's what Vanessa Bell Calloway looked like as Imani Izzi in Coming to America (1988): Paramount Pictures / Courtesy of Everett Collection
Here's what Vanessa Bell Calloway looks like today: Harmony Gerber / Getty Images
Here's what Taye Diggs looked like as Winston Shakespeare in How Stella Got Her Groove Back (1998): 20th Century Fox / Courtesy of Everett Collection
Here's what Taye Diggs looks like today: Jillian Clark / Getty Images
Here's what Rhys Ifans looked like as Spike in Notting Hill (1999): Universal Pictures / Courtesy of Everett Collection
Here's what Rhys Ifans looks like today: Dave J Hogan / Dave J Hogan / Getty Images
Here's what Jessica Alba looked like as Kirsten Liosis in Never Been Kissed (1999): 20th Century Fox
Here's what Jessica Alba looks like today: Steve Granitz / WireImage / Getty Images
Here's what Robert Schwartzman looked like as Michael Moscovitz in The Princess Diaries (2001): Disney / Courtesy of Everett Collection
Here's what Robert Schwartzman looks like today: Anthony Delmundo / Getty Images
Here's what Rajiv Surendra looked like as Kevin G. in Mean Girls (2004): CBS Photo Archive / Getty Images
Here's what Rajiv Surendra looks like today: Here's what Olivia Olson looked like as Joanna in Love Actually (2003): Universal Pictures
Here's what Olivia Olson looks like today: Here's what Sean Marquette looked like as young Matt Flamhaff in13 Going on 30 (2004): Sony Pictures Releasing / Courtesy of Everett Collection
Here's what Sean Marquette looks like today: Here's what Clea DuVall looked like as Graham Eaton in But I'm a Cheerleader (1999): Lionsgate Films
Here's what Clea DuVall looks like today: Stefanie Keenan / Getty Images
Here's what Nia Long looked like as Nina Mosley in Love Jones (1997): New Line Cinema / Courtesy of Everett Collection
Here's what Nia Long looks like today: Manny Carabel / Getty Images
Here's what Morris Chestnut looked like as Lance Sullivan in The Best Man (1999): Universal Pictures / Courtesy of Everett Collection
Here's what Morris Chestnut looks like today: Tommaso Boddi / WireImage / Getty Images
Here's what Adrian Grenier looked like as Nate Cooper in The Devil Wears Prada (2006): 20th Century Fox / Courtesy of Everett Collection
Here's what Adrian Grenier looks like today: Phillip Faraone / Getty Images
Here's what Heather Burns looked like as Christina in You've Got Mail (1998): Warner Bros. Pictures / Courtesy of Everett Collection
Here's what Heather Burns looks like today: Bruce Glikas / FilmMagic / Getty Images
Here's what Joe Torry looked like as Chicago in Poetic Justice (1993): Columbia Pictures / Courtesy of Everett Collection
Here's what Joe Torry looks like today: Harmony Gerber / Getty Images
And here's what Judy Greer looked like as Penny Nicholson in The Wedding Planner (2001): Sony Pictures Releasing
Here's what Judy Greer looks like today: Araya Doheny / Getty Images
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