Whether it’s for a good mood or a bad one, guilty pleasure movies are a great way to boost spirits regardless of the story’s quality or critical admiration, with the 2000s bringing plenty of worthy additions to this genre. The 2000s saw a variety of different movies hit the silver screen, and some of the best are cheesy and feel-good releases that may not have been praised for their stories, scripts, or filmmaking approaches. Although some hemes and messages from these movies might not be seen as much nowadays, the atmosphere they provide can still be widely entertaining.
Filled with bold fashion, cringe-worthy dialogue, and incredible soundtracks, films from the 2000s make a great guilty pleasure option for movie night. Although some of the humor used in movies from the 2000s can be considered a product of the times, there are plenty that have aged like fine wine, and are as relevant now as they were at the time of release. Whether it’s a gripping storyline or the need for some sidesplitting jokes, there are plenty of guilty pleasure movies from the 2000s to enjoy.
10 Shark Tale (2004)
Rotten Tomatoes Score: 35%
Animated DreamWorks film Shark Tale stars Will Smith as a fish named Oscar, who works at the local Whale Wash and dreams of becoming rich and famous. Although generally considered to be quite cheesy, it has a great soundtrack and brilliantly displays Smith’s voice-acting skills. The 2004 movie boasts an incredible star-studded cast other than Smith, including the likes of Jack Black, Robert De Niro, Renée Zellweger, and Angelina Jolie. Despite its commerical success, a Shark Tale 2 was never made, though it still enjoys a lasting legacy as a great guilty pleasure movie.
9 Not Another Teen Movie (2001)
Rotten Tomatoes Score: 31%
The 2001 satire movie Not Another Teen Movie saw Chris Evans in one of his earliest credited appearances on-screen, portraying the popular jock Jake Wyler. The parody takes a lot of inspiration from teen films such as American Pie and Ferris Bueller’s Day Off, and also saw actor Paul Gleason reprise the character of Vice Principal Vernon from The Breakfast Club. Despite only having a 31% rating on Rotten Tomatoes, Not Another Teen Movie is a great “bad” movie filled with purposefully exaggerated acting and goofy humor.
8 She’s The Man (2006)
Rotten Tomatoes Score: 44%
Following the success of Amanda Bynes’ Nickelodeon career, the actress starred in multiple teen films, including She’s the Man. Based on the Shakespearean romantic comedy Twelfth Night, Bynes stars as a high school student pretending to be her own brother, opposite well-known actor Channing Tatum. Despite its source material, She’s the Man takes an ancient story and turns its modern-day retelling into one hundred and five minutes of teenage drama and feel-good hilarity. Though it didn’t fare well with critics, She’s the Man‘s nostalgia establishes it as one of the most unforgettable teen rom-coms of the 2000s.
7 13 Going On 30 (2004)
Rotten Tomatoes Score: 64%
13 Going on 30 saw Jennifer Garner’s first leading role in a film as the older Jenna Rink, a 13-year-old girl who wakes up in the body of her 30-year-old self. A teenage Jenna, stuck in the body of a grown woman, finds herself in a string of hilarious situations she finds herself unequipped to deal with. The film also stars Mark Ruffalo as Garner’s romantic interest, with the role of Matty being one of his most notable breakthrough roles. 13 Going on 30 is considered a cult classic, combining both teenage drama and camp humor, alongside a very 2000s soundtrack.
6 Legally Blonde (2001)
Rotten Tomatoes Score: 71%
Legally Blonde stars Reese Witherspoon as Elle Woods, a young woman who goes from a vapid, materialistic layabout to an independent, strong-willed lawyer. Not only is Legally Blonde filled with feel-good moments nostalgic to the early 2000s, but it also flips stereotypes of women on its head. It also sees Elle gain a new sense of self-respect, being a great example of character development in comedy movies. Given Legally Blonde may not fit everyone’s comedic taste within the larger population, it’s a perfect guilty pleasure movie. Its sequel, Legally Blonde 2: Red, White & Blonde, was released in 2003, and Legally Blonde 3 is awaiting a release date.
5 Hot Rod (2007)
Rotten Tomatoes Score: 39%
Hot Rod saw Andy Samberg’s first film role in 2007, just two years after joining the cast of Saturday Night Live. Samberg stars as an amateur stuntman, who tries to raise some cash with his biggest stunt yet. The film was consistently praised for its use of high-quality comedy, but its story hasn’t reveived similar widespread acclaim over the years. Interestingly enough, Hot Rod was originally drafted by South Park writer Pam Brady as an SNL project for Will Ferrell.
4 Love Actually (2003)
Rotten Tomatoes Score: 64%
The Christmas-themed feel-good film Love Actually has a huge ensemble cast, including the likes of Martin Freeman, Hugh Grant, Andrew Lincoln, and Kiera Knightley, to name a few. The anthological romantic comedy follows a seemingly random group of characters across the world, who all fall in love as their paths cross throughout the festive time. Love Actually was written and directed by British film legend Richard Curtis, the mind behind other famous rom-coms such as Bridget Jones’ Diary, Notting Hill, and Four Weddings and a Funeral. Despite being a Christmas movie, Love Actually‘s guilty pleasure status still applies year-round.
3 Dude, Where’s My Car? (2000)
Rotten Tomatoes Score: 17%
Dude, Where’s My Car? provided Jennifer Garner with one of her first major movie roles, portraying Wanda, the girlfriend of Ashton Kutcher’s lead character Jesse. The stoner film follows two hungover roommates on a search for their car, with the movie’s title frequently referenced in pop culture following its success. Although a lot of the humor in this film may not fly by today’s standards, there are still plenty of hilarious moments for a guilty pleasure watch.
2 A Cinderella Story (2004)
Rotten Tomatoes Score: 11%
A Cinderella Story sees Disney Channel star Hilary Duff in a teenage rom-com adaptation of the classic fairytale Cinderella, opposite 2000s leading man Chad Michael Murray and The White Lotus star Jennifer Coolidge. Much like Legally Blonde, A Cinderella Story sees stereotypes of women turned on its head, as Duff’s character works day-in-day-out to save for college while waiting hand and foot on her step-mother. Despite the film still focusing on a male-female relationship, its final scenes see Murray’s jock character ignore the expectations of his peers and pursue Sam (Duff), regardless of their class differences.
1 High School Musical (2006)
Rotten Tomatoes Score: 67%
Disney franchise High School Musical saw an incredible three films and, in more recent years, a television series. Following the students of East High, a group of teens all following the status quo and boxed into their individual stereotypes decide to break free from their structure, banding together to take part in the school’s spring musical. Although Zac Efron didn’t sing in the first High School Musical, he did lend his voice to the second and third, along with the rest of the belting and passionate cast.
