28 Coming-of-Age Movies From the '90s That Are Sure to Get You in Your Feels

Set in the early 1960s and based on the novel of the same name by Patty Dann, Winona Ryder and Madonna star in this dramedy as 15-year-old Charlotte and her wacky mother, who constantly moves Charlotte and her younger half-sister (who's played by Christina Ricci) around the country. Charlotte is obsessed with Catholicism, uneducated about sex, and totally humiliated by her flamboyant mom, but she must come to accept her family for who they are.

Hip-hop duo Kid 'N Play stars in this cult classic as two high schoolers, one of whom is throwing a party while his parents are away, and another who is desperate to attend, even though his father forbids him from going. In addition to having incredible music, House Party made history by rejuvenating the classic teen party movie and putting Black actors in the starring roles.

Reese Witherspoon stars in this drama as Dani, a 14-year-old girl from Louisiana who experiences her first love and first heartbreak in the summer of 1957 when she meets 17-year-old Court. Once you see Witherspoon in The Man in the Moon (which was her first film role), you'll understand why her career took off after starring in this one.

Set in South Central Los Angeles, this drama tells the story of Tre, who is sent by his mom to live with his dad in Crenshaw after getting into a fight at school. Though Tre's tough-love father instills him with respect and teaches him how to stay out of trouble, his friends don't have the same support at home, and Tre helplessly watches as they're drawn into gang and drug culture. With a cast that includes Ice Cube, Cuba Gooding Jr., Morris Chestnut, Laurence Fishburne, Nia Long, Regina King, and Angela Bassett, you know this one has to be good.

Though we still blame My Girl for our bee phobia, there is no doubt that this drama film is an absolute gift. Centered around 11-year-old hypochondriac Vada and her funeral director father, My Girl will teach you important lessons about navigating teacher crushes, potential stepmoms, and the untimely death of your best friend.

This drama tells the story of Chantel, a 17-year-old growing up in Brooklyn with dreams of leaving her working class neighborhood behind to attend college and eventually become a doctor. However, her dream is tested by her penchant for getting in trouble at school, her boyfriend, and the accidental pregnancy that results from her relationship.

Set in Harlem, Juice revolves around four teens who must contend with police harassment, rival gangs, and the temptation of petty crime on a daily basis. While the leader of the group, Bishop (played by Tupac Shakur), has a gun and a desire to delve into more serious crime, another member, Q (who's played by Omar Epps), has bigger dreams for himself — but Bishop isn't willing to let him ditch their crew that easily.

Set in the 1950s, this sports drama follows David, a working class Jewish teen (played by Brendan Fraser) who gets the opportunity to attend and play football at an exclusive Massachusetts prep school for his senior year. Though he quickly gains popularity among his peers for his football skills, that all changes when his Jewish background is discovered and his new friends (played by Matt Damon and Chris O'Donnell) turn their peers against him.

In this modern retelling of Mark Twain's The Prince and the Pauper, an academically gifted nerd and a tough bad boy (played, once again, by Kid 'n Play) accidentally get their permanent records switched, and they decide to take advantage of the situation. Duncan then relies on Blade to help him pass gym class and earn respect with his classmates, while Blade uses Duncan to help him improve his grades. The result: both teens discover talents they would have never explored otherwise.

Johnny Depp stars in this drama as the titular Gilbert, a small-town 24-year-old stuck at home in Iowa caring for his debilitatingly overweight mother and his 17-year-old brother with mental disabilities (played by Leonardo DiCaprio). However, Gilbert finds his life changed forever when he encounters a free-spirited woman named Becky (played by Juliette Lewis), who helps him finally grow up.

In this drama, an 18-year-old who grew up in the projects in LA desperately searches for a way out of the gang he's fallen in with and a fresh start. Though a caring teacher and his supportive girlfriend try to offer him help, Caine soon discovers that leaving his past life behind won't be as easy as he hoped.

Based on the memoir of the same name by author Tobias Wolff, This Boy's Life is set in the 1950s, telling the story of a young Tobias (played by Leonardo DiCaprio) whose life changes for the worse after his mother falls in love with a violent man (played by Robert De Niro). When it becomes clear that his new stepfather's abusive behavior won't convince him mom to leave, Toby comes up with a plan for escape on his own.

Directed by Ben Stiller (who also appears in the film), this dark comedy revolves around Lelaina (played by Winona Ryder), an aspiring videographer who decides to create a documentary about her and her friends after they graduate from college. Together, Lelaina and her three roommates share their struggles in life and love, and few movies capture the challenges faced by Gen-X youth like this one.

Co-written, produced, and directed by Spike Lee, this semi-autobiographical film takes place in the Bedford–Stuyvesant neighborhood of Brooklyn during the summer of 1973, revolving around nine-year-old Troy and her family of seven. After Troy returns from her aunt's house, where she was sent for an unwilling visit, she's confronted by difficult news, and she has no choice but to face some very adult lessons about death.

This sweet movie is centered on four friends, going back-and-forth between the formative summer of 1970 and the present day, when the four besties are reunited by one of the women's pregnancies. Besides having an all-star cast (which includes Demi Moore, Christina Ricci, Rosie O'Donnell, Rita Wilson, Thora Birch, Melanie Griffin, and Gaby Hoffman), Now and Then covers everything from divorce to death to puberty, and it's sure to tug on your heartstrings.

This cult classic revolves around a group of teenage indie record store employees — including Liv Tyler, Renée Zellweger, Robin Tunney, and Johnny Whitworth — as they try to save their shop from being sold to a major retail chain. Over the course of one epic day, the teens try to recoup the store's losses after one of the employee bets (and loses) a large sum of money at a casino, and you can expect to see lots of crushes and kisses along the way.

Loosely based on Jane Austen's Emma, Alicia Silverstone stars in this one as Cher, a spoiled Beverly Hills princess with a passion for fashion and meddling in the love lives of others. When "tragically unhip" new girl Tai (played by Brittany Murphy) arrives at Bronson Alcott High School, Cher decides to take her under her wing and find her a boyfriend — but unfortunately, the guy who catches Tai's eye just so happens to be the guy Cher has secretly been in love with forever.

Based on Ann M. Martin's novel series of the same name, The Baby-Sitters Club follows a group of girls who decide to create a summer day camp for kids in their Connecticut town. While all facing their own private issues — including an estranged father, a diabetes diagnosis, summer school, and a crush on an older boy — the teens must handle watching over their rowdy charges, which makes for a complicated summer.

Jurnee Smollett (whom you might recognize as Denise from Full House, Jess from Friday Night Lights, or Black Canary from Birds of Prey) stars in this drama as the titular Eve, a girl growing up in 1960s Louisiana whose life changes forever after she accidentally catches her dad cheating with another woman. Over the course of a summer, her dad's serial infidelity comes to light, and Eve realizes that her seemingly perfect family may be nothing more than a facade.

Written by and starring Ben Affleck and Matt Damon, this gem of a movie tells the story of a young MIT janitor whose hidden genius is only recognized after he solves a difficult graduate-level math problem left on the board of a classroom. An MIT professor (played by Stellan Skarsgård) wants to help him reach his potential, but after he attacks a police officer, he must first seek the help of a therapist (played by Robin Williams) to get leniency.

Directed by Wes Anderson, Jason Schwartzman stars in this dramedy as Max, an eccentric prep school teen who develops a crush on a grade school teacher and a friendship with a rich industrialist (played by Bill Murray), whom he turns to for relationship advice. However, things become complicated when Max's new friend ends up wooing the teacher instead, resulting in an all-out war between the two.

Like so many other teen-centric '90s comedies, this flick takes place after high school graduation at a rich classmate's wild house party, where everyone hopes to settle old debts and make new moves before high school is over forever. From a shy outsider hoping to finally confess his crush to the prom queen (played by Jennifer Love Hewitt) to a wannabe desperate to lose his virginity (played by Seth Green), not everyone is successful in their quests, but the result is definitely entertaining.

Drew Barrymore stars in this comedy as Josie, a 25-year-old newspaper reporter who gets a chance to redo her traumatic high school experience when an assignment requires her to go undercover at a local high school. Though she has every intention of shaking off her reputation as "Josie Grossie" and befriending the popular crew, Josie finds herself drawn to the school's outcasts instead . . . as well as her handsome English teacher.

Starring Freddie Prinze Jr. and Rachael Leigh Cook, this rom-com tells the story of Zack, a popular high schooler who bets his friend he can turn the school outcast into the prom queen in only six weeks. During that time, Zack gains her trust, gives her a makeover, and — unsurprisingly — ends up falling for her.

Loosely based on William Shakespeare's The Taming of the Shrew, this rom-com stars Julia Stiles as Kat, a moody teen who's more interested in going to Sarah Lawrence College than dating, unlike her younger sister Bianca, who's desperate to go on a date. When Kat's father decides Bianca can only start dating after Kat does, the guy crushing on Bianca recruits bad boy Patrick (played by Heath Ledger) to woo Kat, as impossible a task as it seems.

James Van Der Beek stars in this sports drama as Mox, an academically gifted football player with dreams of leaving football-obsessed Texas behind and attending Brown University after high school. Unfortunately, his verbally-abusive coach and football fanatic father have very different plans for Mox, and he must decide whether pursuing his goals is worth letting down the authority figures in his life.

What happens when a telesales operative in the midst of a midlife crisis suddenly can't stop looking at his daughter's sexy cheerleader bestie? A family slowly unravels in a majorly dramatic way — and the relationship between Jane and Angela (played by Thora Birch and Mena Suvari, respectively) gets kind of awkward.

In this raunchy comedy — starring Jason Biggs, Seann William Scott, Tara Reid, and Alyson Hannigan, among many others — four high school seniors make a pact to lose their virginity before graduation. Of course, in their quest to have sex, the guys face unexpected challenges and surprises, including first love, horny band geeks, and Stifler's mom.