
Underrated Gems of the 2000s
Photos courtesy of 20th Century Fox and Warners Bros. Pictures.
The 1980s and 1990s brought us films centered around teenagers. The 2000s brought a variety of different films. Popular films from the 2000s include: Mean Girls (2004), Pride & Prejudice (2005), 13 Going on 30 (2004), Love Actually (2003), The Devil Wears Prada (2006), among many others. While there were commercially and critically successful films, there are a few that didn’t get the recognition they deserve.
Here are some underrated gems of the 2000s.
My Big Fat Greek Wedding (2002)
My Big Fat Greek Wedding is a 2002 romantic comedy film that is directed by Joel Zwick. The cast includes: Nia Vardalos, John Corbett, Lainie Kazan, Michael Constantine, Gia Carides, Joey Fatone, and Andrea Martin. Its premise follows Toula Portakalos (Vardalos), a middle class Greek American woman who falls in love with Ian Miller (Corbett) a middle class White Anglo-Saxon Protestant while dealing with her chaotic and overbearing Greek family.
While the film was a box office success making over $360 million, I believe that it’s really underrated. The sequel is underrated too. I actually love the sequel a little more but the original is iconic. The humor in these films is everything. Gus with his Windex cracks me up every time. It’s such a feel-good film that will make you laugh.
Sleepover (2004)
Sleepover is a 2004 teen comedy film directed by Joe Nussbaum. The cast includes: Alexa PenaVega, Mika Boorem, Sara Paxton, Evan Peters, Jane Lynch, Brie Larson, Steve Carrell, and Jeff Garlin. Its premise follows a group of girls who are challenged to a treasure hunt by the school’s popular girl (Paxton) and leads to unexpected romances and a night that changes their lives forever.
The film matched its $10 million budget in the box office. This film deserves so much more love. It’s such a great teen comedy film and features an ensemble cast. It’s almost nostalgic for me when I rewatch this and I honestly don’t know why because I was only 5 or 6 when this came out. As I grew up, I watched it and it reminds me of simpler times.
The Family Stone (2005)
The Family Stone is a 2005 dramedy film directed by Thomas Bezucha. The cast includes: Diane Keaton, Sarah Jessica Parker, Dermot Mulroney, Rachel McAdams, Claire Danes, Craig T. Nelson, Luke Wilson, and Tyrone Giordano. Its premise follows the eldest son, Everett (Mulroney), who brings home his uptight girlfriend, Meredith (Parker), and chaos ensues during the holiday season.
This is one of my comfort films and one of my favorite films of all time. It’s so funny and entertaining. The ensemble cast is great. I love that it doesn’t just focus on Everett and Meredith but other characters as well. Nobody talks about this film enough.
Because I Said So (2007)
Because I Said So is a 2007 romantic comedy film directed by Michael Lehmann. The cast includes: Diane Keaton, Mandy Moore, Lauren Graham, Piper Perabo, Gabriel Macht, Tom Everett Scott, and Stephen Collins. Its premise follows the rollercoaster of a relationship of Daphne (Keaton) and Milly (Moore) and the endless meddling of Milly’s love life.
While critics called the film the worst to come out of 2007 and I think they’re wrong. I don’t think it’s the best film to come out of that year but I love this film. It’s so hilarious and I love the plot. While it’s predictable, it has its moments of unpredictability with other things which I love. The chemistry between Keaton and Moore is so great.
Nancy Drew (2007)
Nancy Drew is a 2007 mystery-thriller film directed by Andrew Fleming. The cast includes: Emma Roberts, Max Thieriot, Rachael Leigh Cook, Tate Donovan, and Josh Flitter. Its premise follows the adventures of teen detective, Nancy Drew (Roberts) as she and her father move to California where a big mystery rises to the surface.
This film brings back so much childhood nostalgia for me. I used to watch this on my portable DVD player when I would go to Disney World as a kid. I still love this film as an adult. I love the entire plot and how different it is when compared to other films aimed at children.
P.S. I Love You (2007)
P.S. I Love You is a 2007 romantic drama film directed by Richard LaGravenese. The cast includes: Hilary Swank, Gerard Butler, Gina Gershon, Lisa Kudrow, Jeffrey Dean Morgan, and Harry Connick Jr. Its premise follows Holly (Swank) mourning the unexpected loss of her husband Gerry (Butler) through a series of letters he wrote to her before he passed away.
While it received mostly negative reviews from critics, it succeeded at the box office making $156.8 million against a $30 million budget. I love the cast in this film as well as the story. It’s heartbreakingly beautiful and it’s interesting to see how Holly changes throughout the film.
27 Dresses (2008)
27 Dresses is a 2008 romantic comedy film directed by Anne Fletcher. The cast includes: Katherine Heigl, James Marsden, Malin Åkerman, Judy Greer, and Edward Burns. Its premise follows a woman, Jane (Heigl), who has been a bridesmaid for 27 weddings but dreams of having her own one day. She meets Kevin Doyle (Marsden) and sparks instantly fly but not in the way you might think.
This is another comfort film of mine. I’ve loved this film for years. I’ve rewatched it so many times at this point but it never gets old. I love the plot, cast, and chemistry between Heigl and Marsden. It’s hilarious and so entertaining.
What Happens in Vegas (2008)
What Happens in Vegas is a 2008 romantic comedy film directed by Tom Vaughan. The cast includes: Cameron Diaz, Ashton Kutcher, Rob Corddry, Treat Williams, Lake Bell, and Jason Sudeikis. Its premise follows the sudden and drunken pairing of Jack (Kutcher) and Joy (Diaz) who get married in Las Vegas and plan to get a divorce when they realize it was mistake. When Jack wins a $3 million jackpot, Joy claims she should get half of the money since they are married. This is when the two start battling each other for the money and something unexpected happens.
This film so funny and the cast is great. I really love the chemistry between Diaz and Kutcher. The comedic relief from Bell and Corddry is everything.
He’s Just Not That Into You (2009)
He’s Just Not That Into You is a 2009 romantic dramedy film directed by Ken Kwapis. The cast includes: Jennifer Aniston, Ginnifer Goodwin, Bradley Cooper, Scarlett Johansson, Drew Barrymore, Ben Affleck, Justin Long, and Jennifer Connelly. Its premise follows the romantic lives of 9 different people.
This film is one of my favorites. I love films like this that focus on multiple characters. I particularly love Gigi (Goodwin) and Alex’s (Long) storyline.
It’s Complicated (2009)
It’s Complicated is a 2009 romantic comedy film directed by Nancy Meyers. The cast includes: Meryl Streep, Alec Baldwin, Steve Martin, John Krasinski, Lake Bell, Zoe Kazan, Hunter Parrish, and Caitlin FitzGerald. Its premise follows single mother and bakery owner, Jane (Streep), as she begins a secret affair with, Jake, her ex-husband, a decade after their divorce. Jane finds herself attracted to her architect, Adam (Martin), and things get chaotic.
My mom introduced me to this film years ago. I love it so much. The camaraderie is so entertaining and the cast is so good.
Final Thoughts
I hope you enjoyed this list of underrated gems from the 2000s. Please give them all a watch if you haven’t already. I promise you won’t regret it.
Please feel free to DM me on my Instagram and let me know your favorite films from the 2000s!

