The 20 Most Underrated Movies Of The ’90s And 2000s

Before we get started, I’m going to apologize rn, because my ’90s and 2000s nostalgia have hit ~peak~ levels. With all of the pressures of adulting, I just wish I could go back to the good ol’ days of laying out sleeping bags on my friend’s living room floor, loading up on Dunkaroos and Surge, and spreading out the Blockbuster movies we rented so we could decide what to watch first. It was all just so much ~simpler~ back then. And don’t even get me started on the movies.

Sure, I could talk about how amazing Clueless and 10 Things I Hate About You are until I’m blue in the face, but there were oh-so-many more movies out there that were just as good but severely underrated. I mean, how could no one see the sheer genius of teenage Reese Witherspoon playing a deranged high school student who will do anything, and I mean annyyyythinggggg, to get voted class president in Election? Or Mandy Moore’s portrayal of a God-fearing, overly-obsessed, judgmental Christian in Saved!? It blows my mind that some of these movies have just slid on by unnoticed.

But not for long, my friends. We’ve rounded up the 20 most underrated movies of the ’90s and 2000s to give these films the proper credit they deserve. (And to ease our nostalgia in the process.)

1. The Man in the Moon (1991)

Starring: Reese Witherspoon, Sam Waterson and Tess Harper

The gist: This is a coming-of-age love story set in the South during the late ’50s, and follows the life of 14-year-old Dani Trant (Witherspoon) as she discovers new love, friendships, and everything else that comes with those complicated teen years.

Best line: “Did’ja ever like somebody so much … that it almost made’ja sick?” — Dani Trant

2. The Baby-Sitter’s Club (1995)

Starring: Rachael Leigh Cook, Bre Blair and Schuyler Fisk

The gist: Seven best friends in junior high, and members of The Baby-Sitter’s Club, host a summer day camp for the kids in their town. This sets the backdrop for the rest of their summer, filled with complicated family relationships, summer school, boys, and more.

Best lines: “You know, we’re more than just a club. We’re friends. Best friends. Nothing could ever change that.” — Kristy Thomas

3. Freeway (1996)

Starring: Reese Witherspoon and Kiefer Sutherland

The gist: This is a twisted take on Little Red Riding Hood set in the ’90s, where 15-year-old juvenile delinquent Vanessa Lutz (Witherspoon) runs away to her grandmother, whom she’s never met, in order to escape foster care. While on the freeway, she picks up this hitchhiker (Sutherland) who turns out to be a psychotic serial killer.

Best line: “I’m pissed off and the whole world owes me. Give me your goddamn money.” — Vanessa Lutz

4. Excess Baggage (1997)

Starring: Alicia Silverstone, Benicio Del Toro and Christopher Walken

The gist: Emily (Silverstone) is a rich brat who’s looking for Daddy’s (Walken’s) attention, so she fakes her own kidnapping and puts out a ransom — not for the money, but to get her father to really notice her. However, her plan goes haywire when an actual criminal (Del Toro) steals the car that she locked herself in. The plan goes even more haywire when Emily finds herself falling for the car thief.

Best line: “Oh, hi Dad, I’m okay but um … Daddy he made me touch his penis.” — Emily

5. All I Wanna Do (1998)

Starring: Kirsten Dunst, Lynn Redgrave, Rachael Leigh Cook and Gaby Hoffman

The gist: Set in the 1960s, five besties discover their all-girls school is combining with the local all-boys school. They’re all for it at first, but once the boys are actually there on campus, they are totally ~not~ having it. What happens next are hilarious pranks and hijinks to get the boys out of their school for good.

Best line: “Up your ziggy with a wa wa brush.” — Odette

6. Can’t Hardly Wait (1998)

Starring: Jennifer Love Hewitt, Ethan Embry, Seth Green and Charlie Korsmo

The gist: The movie centers around one night: a high school graduation party for the class of ’98. One dude wants to get with a girl he’s pined over for years, while another plans to get revenge on his bully. Sex, drugs, partying, and overall hilarity ensues.

Best line: “You know what? Why don’t you go off and get yourself a goddamn life, asshole?” — Amanda Becket

7. Jawbreaker (1999)

Starring: Rose McGowan, Rebecca Gayheart, Julie Benz and Judy Greer

The gist: Three besties planned the ultimate surprise for their friend on her birthday: kidnap her in the early morning while she’s still wearing her pj’s, blindfold her, lock her in the trunk of their car, and surprise her with an early birthday breakfast. (Nothing could go wrong, right?) Well their ~genius~ plan takes a turn for the worse when somehow a jawbreaker gets lodged in their bestie’s throat, killing her. The cover up that happens next is beyond anything anyone in their right mind would think up.

Best line: “The one in the green is Courtney. She was like Satan in heels.” — Fern

8. Dick (1999)

Starring: Kirsten Dunst, Michelle Williams, Will Ferrell and Dan Hedaya

The gist: During a class trip to the White House, BFFs Betsy (Dunst) and Arlene (Williams) wander off and become face to face with the president himself: Richard Nixon (Hedaya). The pair become his official dog-walkers for his pup Checkers, as well as his secret advisors during the Watergate Scandal. What happens next is as ridiculously hilarious as you can imagine.

Best line: “You suck, Dick!” — Arlene and Betsy

9. Drive Me Crazy (1999)

Starring: Melissa Joan Hart, Adrian Grenier and Stephen Collins

The gist: After Brad, the guy Nicole (Sabrina the Teenage Witch Hart) has been waiting to ask her out, suddenly decides to go to their school’s Centennial Senior Prom with a cheerleader from another school, Nicole’s desperate for a date. So much so that she decides to clean up her next-door neighbor, Chase (Grenier), and go with him instead to make Brad jealous. In typical high school fashion, feelings and emotions make this project much more complicated than Nicole thought it would be.

Best line: “Prince Charming’s a dick. Bring on the frogs.” — Nicole

10. Drop Dead Gorgeous (1999)

Starring: Kirsten Dunst, Denise Richards, Allison Janney, Kirstie Alley, Brittany Murphy and Amy Adams 

The gist: Before Miss Congeniality, we have these gals of a small Minnesota town fighting for the top spot in the annual beauty pageant. Explosions, falling lights, trailer fires, and death are all apart of this hilarious story of the lengths women will go to to claim the title, Beauty Queen.

Best line: “This pageant is like a roach motel. Girls check in but they don’t check out.” — French fry girls

11. Election (1999)

Starring: Reese Witherspoon, Matthew Broderick and Chris Klein

The gist: In this dark comedy,Tracy Flick (Witherspoon), a high-school over-achiever who’s determined to become student class president, wreaks havoc on the personal life of her teacher, Mr. McCallister (Broderick), as the election draws near.

Best line: “Good morning, Mister M. Looks like you could use a cupcake!” — Tracy Flick

12. Josie and the Pussycats (2001)

Starring: Rachael Leigh Cook, Tara Reid, Rosario Dawson, Alan Cumming and Parker Posey

The gist: After their rock band makes it big, the girls of the band, Josie and the Pussycats, come to realize that the studio they’re working for has been sending subliminal messages through their music. A must-watch for the mere number of cameos made in this film.

Best line:“Wyatt, you messed with the wrong pussy!” — Valerie

13. Get Over It  (2001)

Starring: Kirsten Dunst, Ben Foster, Shane West, Mila Kunis, Martin Short and Sisqo

The gist: This modern version of A Midsummer Night’s Dream focuses on a basketball star (Foster) who gets dumped by his girlfriend, and follows her into the school play to try to win her back. What happens next is a love triangle filled with singing, dancing, and all-around great humor.

Best line: “She was the first girl to see me naked. Granted we were 7 years old at the time, but I had a feeling, even then. There’s really something about the first girl you play doctor with. Maybe it’s cosmic or something. Or perhaps it’s just that she’s seen your package and didn’t run away screaming.” — Berke Landers

14.  Abandon (2002)

Starring: Katie Holmes, Benjamin Bratt and Charlie Hunnam

The gist: After millionaire college student Embry Larkin (Hunnam) is still missing after two years of silence, Detective Wade Handler (Bratt) is assigned to the case. His first visit is to Embry’s ex-girlfriend, Katie Burke (Holmes), who is under a lot of pressure to finish her college thesis while working at a prestigious company and meeting weekly with her psychiatrist. Katie and Detective Handler find they are mutually attracted to each other, but then Embry reappears, and soon after the Detective goes missing. What happens next is something you’ll never see coming.

Best line: “I won’t make stupid threats but your not gonna run away with this guy because wherever you go, I can follow you…. even if it’s to the woods in New Hampshire.” — Embry Larkin 

15. How to Deal (2003)

Starring: Mandy Moore, Allison Janney, Peter Gallagher, and Trent Ford

The gist: This story focuses on the life of Halley Martin (Moore), a high school student who is so disillusioned by love that she truly doesn’t believe it exists. Watching the dysfunctional relationships of her lonely, divorced mother (Janney), her dad (Gallagher) and his new (much younger) girlfriend, and her sister who is wedding-obsessed only confirms her suspicions of love. But then a freak accident has her meeting quirky Macon Forrester (Ford), and she soon starts questioning everything she thought she knew about life and love.

Best line: “The quickest way to ruin a relationship with someone is to actually try to have a relationship with them.” — Halley Martin

16. 13 Going on 30 (2004)

Starring: Jennifer Garner, Mark Ruffalo and Judy Greer

The gist: Jenna Rink (Garner) makes a wish on her 13th birthday that she’ll be 30, flirty, and fabulous. Hot damn if she doesn’t wake up the next morning and finds she’s been thrown into the future and is a 30-year-old “It” girl working at the popular woman’s magazine Poise. But as she goes about her 30-year-old days, she discovers she’s not the type of person she thought she’d be.

Best line: “I like your dress.” – Becky // “That’s because I have these incredible boobs to fill it out!” – Jenna Rink

17. Saved! (2004)

Starring: Mandy Moore, Jena Malone, Macaulay Culkin, Patrick Fugit and Eva Amurri Martino

The gist: During the summer before their senior year at a Christian school, Mary’s (Malone’s) boyfriend tells her he’s gay. Thinking that God would want her to sleep with him to ~turn him straight again~, Mary does just that. And becomes pregnant. As word slowly gets out among her friends about her ~condition~, Mary finds herself ostracized and demoralized.

Best line: “Burn in hell, you narrow-minded, tacky-ass bitch!” – Cassandra

18. Chasing Liberty (2004)

Starring: Mandy Moore, Jeremy Piven, Mark Harmon, Annabella Sciorra and Matthew Goode

The gist:  Another one for Mandy! First daughter Anna Foster (Moore) has had zero privacy her entire teenage life, and she’s ready for a change. She convinces her dad – the President (Harmon) – to allow her to go to a concert in Prague with just ~two~ agents (Piven and Sciorra). But after she finds out her dad reneged on his promise, she flees the Secret Service and runs off with a gorgeous photographer (Goode). She doesn’t tell him who she really is on their journey to the Love Parade in Berlin, but little does she know that he’s been keeping secrets too. Fun fact: Compare to Katie HolmesFirst Daughter, which came out the same year. They’re strikingly similar.

Best line: “Naked virgin safely in bed.” – Anna Foster

19. Elizabethtown  (2005)

Starring: Kirsten Dunst, Orlando Bloom, Susan Sarandon, Alec Baldwin, Judy Greer, Jessica Biel and Bruce McGill

The gist: After Drew Baylor (Bloom)  is fired from his swanky corporate job as a shoe designer for losing the company $1 billion, he gets even worse news: his father has passed away. On his plane ride to Kentucky to arrange his father’s memorial service, he meets a quirky airplane stewardess named Claire Colburn (Dunst), and she quickly changes his life in the most incredible way.

Best line: “You deserve a guy who says: ‘I can’t imagine a world with you.'” – Drew Baylor

20. Whip It (2009)

Starring: Ellen Page, Drew Barrymore, Kristen Wiig, Jimmy Fallon and Marcia Gay Harden

The gist: Bliss Cavendar (Page) has always felt like a misfit. While her mom (Gay Harden) has dreams of her winning a beauty pageant, Bliss doesn’t see that for herself ~at all~, and is struggling with her identity. And then she discovers a women’s roller derby league near her hometown in Austin, Texas. She joins the team and finds she’s whip fast, but keeping this from her mother is going to be harder than she thinks.

Best line: “Screw you and your grandmother’s Chevy Celebrity!” – Bliss Cavendar

21. He’s Just Not That Into You (2009)

Starring: Jennifer Aniston, Jennifer Connelly, Bradley Cooper, Ben Affleck, Justin Long, Scarlett Johansson, Drew Barrymore, Busy Philipps and Ginnifer Goodwin

The gist: We follow along with the interconnected stories of several different relationships and the drama that unfolds in each of them. All of these characters somehow intertwine into the life of Gigi Haim (Goodwin), who’s looking for her prince charming amid plenty of bad dates. The film looks at how we often misread human behavior in our dating and love lives

Best line: “I may dissect each little thing and put myself out there so much but at least that means that I still care. Oh! You’ve think you won because women are expendable to you. You may not get hurt or make an ass of yourself that way but you don’t fall in love that way either. You have not won. You’re alone. I may do a lot of stupid shit but I’m still a lot closer to love than you are.” –Gigi Haim

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