Do you want to “ruin” your day by procrastinating and getting nothing done at all? Then this list is for you. For fans of Heathers, The Fifth Element, Hocus Pocus and Disney Channel movies, I hope you didn’t plan to do anything else other than watch movies for the next 50 hours of your life.
One of the greatest cult comedies ever made and the movie that helped give life to Mean Girls. Heathers features a never-better Winona Ryder and some of the most quotable lines in the history of man (e.g. “What’s your damage?”, “My bullshit teen angst has a body count,” and “Fuck me gently with a chainsaw.”) Also, this movie is proof that monocles need to make a comeback. Get on it, Ralph Lauren. (Also streaming: the 1994 cult indie comedy Threesome.)
Still Danny Boyle’s best movie and a fantastic adaptation of the Irvine Welsh novel. This movie has everything: a sharp yet melancholy script, fine performances from its then up-and-coming cast (Johnny Lee Miller, Ewan McGregor and Kelly MacDonald) and one of the great movie soundtracks. And you get to see Ewan McGregor’s penis, which is always worth the price of admission in itself.
3. Hocus Pocus
A cult movie phenomenon and a nostalgic favorite around Halloween. Infinitely quotable, Hocus Pocus has inspired a million Tumblr memes and drinking games (take a shot every time they say the words “virgin,” “witch,” or “magic”). This movie is still Bette Midler’s favorite role and features some of The Divine Miss M’s most deliciously over the top mugging. And the scene with Kathy Najimy in “the devil’s house” is just classic.
4. Gosford Park
One of Robert Altman’s best films and proof that the master never lost his touch for witty dialogue and overlapping narratives. Gosford Park features a dizzying array of British and American actors and boasts Maggie Smith, Helen Mirren, Kristin Scott Thomas, Clive Owen, Bob Balaban, Kelly MacDonald, Stephen Fry and Michael Gambon at their sharp-tongued best. Screenwriter Julian Fellowes would go onto rework many of these same elements in Downton Abbey, allowing Maggie Smith to play virtually the same character she did in Gosford Park.
A terrible, terrible movie. (I mean, technically.) However, Overboard also happens to be absurdly watchable, mostly due to screen goddess Goldie Hawn’s magic touch. Hawn plays a spoiled heiress who gets down with the blue-collar ways, thanks to Kurt Russell’s muscles. Hawn and Russell have been together for the last thirty years, and with chemistry like this, you can see why. This movie is always playing on cable somewhere, because it costs about five cents to broadcast.
6. Gangs of New York
An often-overlooked entry in Martin Scorsese’s late period that’s at turns spellbinding and frustrating. Gangs of New York took Scorsese twenty years to get off the ground and because of that, Scorsese had to settle on the wildly miscast Cameron Diaz and Leonardo DiCaprio, instead of Robert DeNiro and Meryl Streep. But Diaz’s hair issues aside, Gangs features Daniel Day-Lewis’ best performance as Bill the Butcher, a character that still gives me nightmares ten years later.
7. When Harry Met Sally
The crown jewel in the late Nora Ephron’s work and the movie that birthed the modern romantic comedy. When Harry Met Sally is close to perfect, thanks to Ephron’s warm and funny script and a perfectly matched Billy Crystal and Meg Ryan and an underrated supporting performance from Carrie Fisher. Has Meg Ryan ever been more grounded and lovable than she was here? Ryan spent years chasing other romantic vehicles, but never found anything half as great at this.
8. Zenon: Girl of the 21st Century
Arguably the Disney Channel’s most enduring entry from its golden years of made-for-TV movies and a great Halloween costume choice every year. (In particular, Proto Zoa is always a big hit at parties.) Zenon features lovably spunky performances from Sister Act’s Raven-Symone and Kirsten Storms, who later appeared in Johnny Tsunami, another Disney favorite. Everything about this movie is so wonderfully late 90s — from its boy band soundtrack to the pervasive pigtails and blinding neon aesthetic. It’s like a very tiny capsule that speaks in futuristic English. Zedis lapedis!
9. The Fifth Element
A pop sci-fi masterpiece from Luc Besson, the man who also brought us Taken, La Femme Nikita and Leon: The Professional. Everything in this movie is like Lady Gaga’s wet dream, with its outré Gauthier fashions and dada hairstylings. This film features a lot of the things that its actors do best, like Gary Oldman’s hammy scene chewing, Chris Tucker’s mile-a-minute line readings and Bruce Willis just bein’ Bruce. (Also streaming: District 9.)
An underrated entry in the Meryl Streep canon — from back in the late 80s when Meryl decided to cut loose and start having some fun. Streep plays the rich bitch who steals Rosanne Barr’s husband (played by Ed Begley Jr.), and the movie blatantly foreshadows her Devil Wears Prada turn as Miranda Priestly. Anyone who was surprised that someone as sweet and down-to-earth as Streep could play such a dragon lady never saw She-Devil. And as much as I love Meryl in prestige pictures, it’s entertaining to see her apply her chameleonic craft and unparalleled work ethic to fluff. To quote her character, “these are the moments that make life worth living.”
The last great Guy Ritchie movie before he married Madonna and un-learned how to make movies, although the Sherlock Holmes films were a step in the right direction. High on style and kinetic plot twists, the film is a riff on the same formula he established with Lock, Stock and Two Smoking Barrels (and likewise features Jason Statham and Vinnie Jones). Although many critics chided Snatch for its similarities to Lock, it’s like hearing another great rendition of a pop song you love. This one just had Brad Pitt in it.
12. Wish Upon a Star
Another entry in Disney’s lucrative body-switching genre and a delicious 90s cheesefest. Wish Upon a Star is by no means a classic, but it features an incredibly likeable performance from future “scream queen” Danielle Harris and a very young Katherine Heigl, who plays Harris’ mean girl older sister that she trades lives with. It’s like Mean Girls mashed up with Freaky Friday. (Also streaming free online: Smart House and Model Behavior.)
13. His Girl Friday
In my opinion, the sharpest, fastest and funniest comedy ever made. The script for His Girl Friday was so famously verbose that in order to fit in all the dialogue, director Howard Hawks had all of actors step on each others’ lines by starting to speak before the other finished. With its breakneck speed and fiery wit, His Girl Friday is the quintessential screwball comedy and so layered that you can watch it ten times and still pick up on more jokes.
14. The Babysitters’ Club
A must-watch for any kid that grew up with the beloved series of novels. The film version of The Babysitters’ Club is mostly forgotten about and wasn’t a financial success at the time, despite receiving solid reviews. The film blends a dream cast for 90s kids — including Larisa Oleynik (Alex Mack), Raechel Leigh Cook (She’s All That), Schulyer Fisk (Snow Day), Marla Sokoloff (Full House) and Kyla Pratt — along with Ellen Burstyn, Bruce Davidson and Brooke Adams. The Babysitters’ Club stands along with Now and Then as one of the best “friends forever” movies of its era.
15. Not Without My Daughter
A hot mess of a movie if there ever were one. Everything about NWMD is kind of a beautiful nightmare, from Sally Field’s way-over-the-top performance to the heavy-handed script, tone-deaf direction and the ludicrously overt racism. (Muslim groups freaked out upon the film’s release, for good reason.) However, the movie has become something of an in-joke and a punchline since its release (Arrested Development memorably lampooned it), and it’s a must-see for any fan of truly bad cinema.
16. My Big Fat Greek Wedding
An indie darling so ludicrously likeable that it powered its way to being the highest-grossing romantic comedy of all time. Nia Vardalos’ script is a rambunctious riff on second-generation Greek-American identity, and the movie is incredibly relatable for anyone with a big, fat, crazy family. Even though I’m not Greek (sup, Italy?), that movie is my family, because it’s everyone’s family.
17. Sweet Home Alabama
Not a great movie by any stretch of the imagination, but the perfect movie for when you’re drunk on a plane or bored at home on a Tuesday night. (This is why it’s become a cable favorite.) Sweet Home Alabama smartly banks on Reese Witherspoon’s girl-next-door appeal and features a couple great scenes and zingers (e.g. “You brought a baby… into a bar?”) And after gazing into Josh Lucas’ baby blues, you can’t help but give in to the movie’s southern charm. Resistance is futile. (Trivia: Look out for Dakota Fanning as young Reese Witherspoon.)
Hugely unheralded comedy starring Michelle Williams and Kirsten Dunst in her Virgin Suicides days. As described by Leonard Maltin, the movie is a “cross between Clueless and All the Presidents’ Men,” about two air-headed 15-year-olds who accidentally witness Watergate. Dick acts a wonderfully tongue-in-cheek revisionist history and features great cameos from SNL and Kids in the Hall cast members and a post-My So Called Life Devon Gummersall.
19. Some Like It Hot
Listed at #1 on AFI’s list of the greatest comedies of all time and proof that Marilyn Monroe really could act. Tony Curtis and Jack Lemmon shine as Hollywood’s best cross dressers, but the real hero of the film is Billy Wilder’s script. Make sure to keep watching all the way to the closing credits, as Some Like It Hot saves its best gag for last.
20. Sabrina the Teenage Witch: The Movie
A bizarre alternate universe version of Sabrina the Teenage Witch that served as the sorta pilot for the future series. For fans of the TV show, the movie that preceded it is a glimpse into a universe where Sabrina’s real last name is Sawyer, Caroline Rhea doesn’t exist, Salem is British and Sabrina has the naughty hots for a Nick-Carter-haired Ryan Reynolds, who looks about twelve in this. It doesn’t hold a candle to the show that came after it and the production values are atrocious, but the film does explain why Susan Lucci was denied an Emmy all those years: magic!
21. Charlie’s Angels: Full Throttle
A fun and frothy send-up of the classic TV series that succeeds by not taking itself too seriously. Although flawed, the Charlie’s Angels movies were a lot like the series that inspired it: kitschy and smart-dumb, with great energy and a game cast — especially Lucy Liu at her sauciest. Besides, any movies that make room for scene-stealing turns from Sam Rockwell, Tim Curry, Kelly Lynch, Demi Moore, Justin Theroux and Crispin Glover more than pass my muster.
22. Kung Fu Hustle
An enjoyably daffy action import that never quite got the cult it deserved. As described by Roger Ebert, Kung Fu Hustle was “Buster Keaton and Jackie Chan meet Quentin Tarantino and Bugs Bunny.” For the uninitiated, that still doesn’t explain the half of it. Stephen Chow’s martial arts universe is a world in which the laws of gravity and logic don’t exist, like a live-action cartoon version of Crouching Tiger, Hidden Dragon. It’s crazy in the best possible way.
A scattershot but charming send-up of European culture featuring more stereotypes about Europe than you could shake a baguette at. EuroTrip was co-directed by Alec Berg, Jeff Schaffer and David Mandel, three of the many minds behind Seinfeld, and attempts to use the show’s observational humor to say that “Europeans do the darndest things!” The problem is that most of its target audience hasn’t been to Europe, so the film has to rely on barn-door broad stereotypes, like that Europeans are randy and do a lot of drugs. Although it doesn’t work all the time, when it’s on, it’s ON — like in the Bratislava sketch, the film’s highlight. Also, the film features a bonkers good performance from a bald Matt Damon, who plays the punk rock singer who steals Scott Mechlowicz’s girlfriend. (Note: I still know people who have “Scotty Doesn’t Know” as their ringtone.)
24. Layer Cake
Great but overlooked 2005 gangster thriller freshly relevant because of its A-list pedigree. There are a number of reasons to see Layer Cake, yet another movie on this list deserving of a wider following, but the two biggest ones are its stars and director. The movie features before-they-were-famous turns from Tom Hardy, Sally Hawkins, Ben Whishaw, Sienna Miller and Daniel Craig, who landed the role of James Bond in the rebooted series because of his performance here. Layer Cake sees Craig already in full-on-Bond mode: sexy and smooth with an undercurrent of matter-of-fact ruthlessness. The film also launched the career of its director, Matthew Vaughn, who went on to direct Kick-Ass and X-Men: First Class and is widely rumored to take over the new Star Wars trilogy.
25. Romy and Michelle: In The Beginning
The prequel to Romy and Michelle’s High School Reunion, which I didn’t know existed until right now. Seriously, was anyone aware that this was a thing? It aired on ABC Family and featured a slightly pre-Grey’s Anatomy Katherine Heigl, who (clearly) was no stranger to the made-for-TV movie, and Paula Abdul (for some reason). All I know is that I’m watching it ASAP.