New York native and actress Julia Stiles was just 20-years-old when she was cast as Kat Stratford -- the smart, non-conforming high school student -- in the 1999 romantic comedy film "10 Things I hate About You."

Stiles shared the big screen with Heath Ledger as the handsome weirdo, Patrick Verona, Joseph Gordon-Levitt as the sweet and selfless new student, Cameron James, Gabrielle Union as the rude pot-stirrer, Chastity, and Allison Janney as the comedic yet disciplinary high school principal, Ms. Perky.

Julia also played Sara in the 2001 film "Save The Last Dance."

American comedian and actress Judy Greer is well known for playing the role of Penny -- the funny yet instrumental wedding planner that ultimately pushes her co-worker to date, fall in love and get married -- in the 2001 film "The Wedding Planner."

Greer shared the big screen with other A-listers Jennifer Lopez as the wedding planner, seeking monogamy and love, Mary Fiore, Matthew McConaughey as a pediatrician, and ultimately Mary's love interest, Dr. Steve Edison and Justin Chambers as Mary's childhood boyfriend and her secondary option for marriage, Massimo.

And, don't forget her iconic role in "13 Going On 30" with Jennifer Garner!

New York native Héctor Elizondo was no stranger to the cameras when he landed the role of Barney Thompson -- the hotel concierge of The Beverly Wilshire Hotel in Beverly Hills -- in the classic 1990 romantic comedy "Pretty Woman."

Héctor shared the big screen with A-list actors including Richard Gere as the successful millionaire businessman, Edward Lewis, Jason Alexander as the creepy lawyer, Philip Stuckey ... and of course Julia Roberts as the lady of the night who turned into the ultimate love interest, Vivian Ward.

Héctor is also known for his roles in "Chicago Hope," "Runaway Bride," "Young Doctors In Love" and "Georgia Rule."

American-South African actress Embeth Davidtz was 30 years old when she was cast as Miss Honey -- the gentle, caring teacher at Crunchem Hall who ends up adopting one of her students from their mean and careless family -- in the 1996 family film "Matilda."

Davidtz shared the big screen with Mara Wilson as the intelligent daughter who is mistreated by her parents, Matilda, Danny DeVito as Matilda's neglectful father, Harry Wormwood, Rhea Perlman as the bingo-playing mother, Zinnia Wormwood and Pam Ferris, as the cake-lovin', cranky teacher, Miss Trunchbull.

Harvey Fierstein was 40 years old when he played Uncle Frank -- the man responsible for helping magically transform his brother, Daniel, into an elderly housekeeper so he could see his kids -- in the classic 1993 family film "Mrs. Doubtfire."

Fierstein was cast alongside the legendary Robin Williams as the father and recent divorcee trying to make up for his childish behavior, Daniel Hillard, Sally Field as the mother who finds herself wanting a divorce from her husband, Miranda Hillard, and Pierce Brosnan as the new man in Miranda's life, Stu.

American actress Amy Yasbeck was 31 years old when she was cast as Peggy Brandt -- a news reporter who ends up outing the mystery man underneath the green mask - in the 1994 comedy/fantasy film "The Mask."

Amy shared the big screen with A-lister Jim Carrey as a bank teller and main protagonist, Stanley Ipkiss, Cameron Diaz as a singer of the Coco Bongo and love interest of Ipkiss, Tina Carlyle, Peter Riegert, the lieutenant who is on "The Mask" mystery case, Mitch Kellaway and Peter Greene, the main antagonist who is plotting to rob Stanley's bank, Dorian Tyrell.

"It's Showtime!"

Japanese actress and singer Youki Kudoh was 36 years old when she was cast as the 'dragon lady' aka Jasmine -- the main antagonist and assassin with many superpowers like convincing, manipulating and seducing Lee before attempting to murder him -- in the 2007 action/comedy film "Rush Hour 3."

Youki shared the big screen with no other than Jackie Chan as Lee, Chris Tucker as Carter, Hiroyuki Sanada as Kenji and Noémie Lenoir as Genevieve.

"Would you like to know a secret cop? Someone's going to die here tonight."

Minnesota-native Seann William Scott was only 23 years old when he landed the role of the 4/20 friendly Chester -- one of two best friends who set off on an epic adventure to find their car after a wild night of partying -- in the 2000 stoner masterpiece "Dude, Where's My Car?"

Scott was cast alongside Ashton Kutcher as Chester's pothead BFF, Jesse ... and Jennifer Garner and Marla Sokoloff as the twins girlfriends, Wanda and Wilma.

And if your struggling from some smoke-induced memory loss ... Seann William Scott is also known for his legendary character Steve Stifler in the 'American Pie' films.

Duuuude, Sweeeeeet!

New York-based actor Rajiv Surendra is best known for playing the role of Kevin Gnapoor -- captain of The Mathletes ... a club suited for so-called 'math nerds' at North Shore High School -- in the iconic 2004 film "Mean Girls."

Surendra shared the big screen with some of Hollywood's biggest names including Lindsay Lohan as the new girl, Cady Heron, Tina Fey as the calculus teacher and supposed drug dealer, Ms. Norbury, Rachel McAdams as the snobby, popular chick, Regina George, Amanda Seyfried as the not-so-smart girl, Karen Smith ... and Amy Poehler as Regina George's hot cool mom, Mrs. George.

Australian actor Adam Garcia was 28 years old when he was cast as Kevin O'Donnell -- the love interest and male lead who is struggling to make ends meet living in New York City and holds numerous odd jobs including a comic book collector -- in the 2000 bar-stomping cinematic masterpiece "Coyote Ugly."

Adam Garcia shared the big screen with Piper Perabo as Violet Sanford, John Goodman as Bill and Violet's father, LeAnn Rimes as herself and Tyra Banks as Zoe ... one of the Coyotes.

In the words of Mr. O'Donnell himself ... "Have a nice day!"

American singer and songwriter Jewel grabbed the ears and hearts of the world when she released her debut album "Pieces of You" which landed in the number four spot on the U.S. Billboard 200 list and featured hit songs "Who Will Save Your Soul" "Foolish Games" and "You Were Meant For Me."

Jewel continued her success as the guitar-strumming songstress and has 4 grammy nominations to show for it! She came out with her fifth studio album, "0304" in 2003, which spotlighted the popular song "Intuition" ... and is currently preparing for a big U.S. tour this summer.

New York actor Chad Michael Murray was 22 years old when he landed the role of the popular jock Austin Ames aka 'Nomad' -- who winds up steering away from his father's plan for him to play professional football and instead scoops up his Cinderella -- in the 2004 high school movie "A Cinderella Story."

Chad was joined on the big screen with some big Hollywood names including Hilary Duff playing modern-day Cinderella, Sam, Jennifer Coolidge as the evil yet comedic step-mother, Fiona and Regina King as Sam's saving confidant, Rhonda.

London native and singer Jay Sean took over 2009 with his breakout album "All Or Nothing" ... which included the hit singles "Down" and "Do You Remember."

The popular songs topped the Billboard Hot 100 making Sean the first solo artist of South Asian descent to achieve such greatness, but 2009 was a big year for the British artist for other reasons ... he also tied the knot to singer and model Thara Natalie.

The couple's family grew in 2013 when they added a daughter to their impressive list of creations.

"Baby, are you down, down, down, down, down?"

Musician and American actress Fairuza Balk was just 23 years old when she played Vicki Vallencourt - the girlfriend who's a ride or die for her 'geek' of a boyfriend -- in the 1998 football film "The Waterboy."

Balk was cast alongside some of the greats including Adam Sandler as momma's boy and H20 enthusiast turned all-star player, Bobby Boucher, Kathy Bates as Bobby Boucher's overprotective mother, Mama Boucher, Rob Schneider as the annoying yet supportive "you can do it" character, Townie and Henry Winkler as the convincing coach, Coach Klein.

The OG of the OC Stephen Colletti brought the best out of high school surfing, girls, reality (well that's questionable) and straight-up DRAMA from his days on MTV's "Laguna Beach."

Known as the beach town's hot surfer boy, he was the instigator of one of the most iconic high school love triangles which obvi included himself, the sassy hot junior Kristin Cavallari and the quiet wholesome senior girl, 'LC' aka Lauren Conrad.

Stephen would later go on to act in shows like "One Tree Hill," "Hit the Floor," and was Taylor Swift's love interest in her music video "White Horse."