The Wizard of Oz (1939)
Let me take a moment to run down a few of the reasons why this movie is absolute perfection:
1. Judy Garland. Moved from the Midwest to the big city. Child star. Nervous breakdown. Suicide attempt. Wins all the awards. Five husbands. Births Liza Minelli. Dies young. I’m totally glamorizing a really intense, complex, and troubled life, but Judy Garland basically invented the troubled Hollywood starlet, so props where they are due.
2. It’s a secret musical. Well, I mean, nobody is trying to hide the fact that there are songs in the movie, but it isn’t the kind of movie that when you suggest it, some dweeb whines, “UGH NO I HATE MUSICALS.” The movie itself is good enough that even people who don’t like musicals (WHO ARE THESE PEOPLE?) can still enjoy it.
3. It is a movie for everyone. When I was six, The Wizard of Oz was the scariest thing I’d ever seen in my entire life. I watched it all the time, but always with my finger on the VCR’s fast-forward in case any flying monkeys appeared. At 20, I still love this movie. Everything about it is so bizarre, but in a way where you’re never quite sure if the creators even knew this when they were making it. I mean, fairy tails are weird, but The Wizard of Oz is downright freaky.
4. ILLUMINATI. And chemtrails and the gold standard and stuff about the Cold War and atheist propaganda. Basically every conspiracy theory that’s ever been dreamed has been linked to The Wizard of Oz. At this point, I wouldn’t even be that shocked to hear someone assert that the Cowardly Lion shot Kennedy.
5. The colors. This movie is just so damn pretty. —Jamie

The Little Mermaid (1989)
If someone told me that I could only watch one Disney animated musical for the rest of my days, first, I’d wonder why this person had such a tyrannical attitude about cartoon cinema, but then, I’d pick The Little Mermaid—of all the Disney classics it has the best soundtrack (“Kiss the Girl” is my jam), the most attractive prince, and the villain with the most tentacles. Ariel, the titular teenage fish-human hybrid, leads a charmed life. She’s a princess with killer bangs, lives “under da sea,” and has whozits and whatzits galore. But who cares? No big deal. She wants mooore! “More” for Ariel is a life on land where she can spend a day warm on the sand, explore the shore from above, and no longer have to deal with the constant chafing that comes with wearing a shell bra. The Little Mermaid is fun to sing along to—that’s a given—but it’s also inspirational. The story is all about breaking free from the protective bubble that you’ve grown up in. —Amber

The Truman Show (1998)
Jim Carrey plays Truman Burbank, who lives in a seemingly idyllic town—the kind depicted on ’50s shows like Leave It to Beaver—and unwittingly provides constant televised entertainment, from the moment of his birth, to millions of people around the world. He eventually begins to notice that things are a bit off, and starts to question the reality (or lack thereof) around him, all the while being watched over by a super-creepy beret-wearing Ed Harris, who gets to say things like, “Cue the sun,” and control every aspect of Truman’s existence. Like the many reality-TV stars who have found themselves turned into packaged, tightly edited products in the 14 years since the movie’s release (some much more willing than others), Truman struggles with the reality of “reality,” and tries to reconcile his true self with the life that has been painstakingly molded by the great production team in the sky. Jim Carrey is perfect in this movie, and his final scene makes me cry every single time. It’s the kind of movie that makes you question fate, reality, advertising, the people around you, and life in general. It is funny, sad, and beautiful, and perhaps impossible to make in today’s world, where everyone knows that people have “personal brands” to push or whatever. It’s easy these days to become a minor celebrity, to sign up for The Bachelor part 897 and try to jumpstart your career, or sign on to YouTube and carefully orchestrate the image you want to show the world—so to watch a someone trying to escape the box, as opposed to sacrificing everything to get into it, is a quiet and lovely thing. —Pixie

La Dolce Vita (1960)
Pillow fights and fake religious revelations, dancing in Trevi Fountain and fishing for a fantastic sea monster—Federico Fellini’s late-’50s Rome looks like a surreal paradise. The tension between the legendary Swedish goddess Anita Ekberg and the Italian dandy Marcello Mastroianni could have made an exciting love story, but this movie is no Roman Holiday—it’s three hours of pure chaos, more exhausting than the wildest all-nighter. You feel relieved when it ends, but it sticks in your head for the whole next day. —Emma D.

Valley of the Dolls (1967)
Ooh, boy. Let’s start by noting that this film is an adaptation of Jacqueline Susann’s best-selling novel, which Nicole Cliffe breaks down for you perfectly over at The Awl. The film is a total mess, but what a mess it is: every single costume is perfect, every set is amazing, and the pacing is both trippy and dreamy (at times it’s a bit too slow, mostly in the beginning, before everyone gets hooked on “dolls” [pills!] and loses their effing minds). Visually, it’s a bit like an episode of Mad Men as directed by Sofia Coppola with a fever of 103. All of your standard fame clichés are in play—addictions, affairs, women being reduced to their bodies, rehab, the arrival of the understudy—the point being that the glamour of Hollywood hides some pretty dark secrets, which, duh. The moral of the story, basically, is don’t do drugs. Or get into showbiz. Or leave your hometown. Or marry someone without really knowing them. Or date some guy who doesn’t really love you. Or go to France to make “art films.” Because ultimately, fame’s a bitch, and one day, she’s going to show up at your party, snatch the wig off of your head, and throw it in the toilet, where it won’t even flush. —Pixie

The Fresh Prince of Bel-Air (1990-1996, NBC)
In this classic ’90s sitcom, Will Smith plays a fictionalized (but I’d imagine, equally fresh) version of himself. He’s a streetwise kid from West Philadelphia whose “life gets flipped, turned upside down” when his mother sends him to California to live with wealthy relatives—the Banks family. The Bankses may have a mansion and a butler, but idyllic Bel-Air would be lame without its new prince, who rocks his prep school blazer inside out, wears his neon hats sideways, and is liable to start doing the running man without warning. As a person who lives on the planet, you’re basically required to memorize the words to the Fresh Prince of Bel-Air theme (case in point: both my mom and Neil Young as played by Jimmy Fallon know the song). So, if you’ve never seen this show, you need to watch it just to get those lyrics down (it will prove more useful than knowing algebra, I’m pretty sure). But you should also take a look at this show because it will bring you immeasurable joy—Will Smith is so charming that it’s physically impossible not to smile while watching him. —Amber

Mildred Pierce (2011, HBO)
Todd Haynes adapted this quiet, heartbreaking masterpiece almost word-for-word from the original 1941 novel by James M. Cain. Kate Winslet (solid) plays the self-sacrificing Mildred, and Evan Rachel Wood (who I have an odd fascination with) plays her spoiled, wretched nightmare of a daughter (perfectly cast). The miniseries is set in the Great Depression, and this gal becomes a brilliant businesswoman, working her fingers to the bone making pies, waitressing, opening up her own wildly successful restaurant (fried chicken and waffles), then opening a whole chain—all for her awful daughter. I love the 1940s sets and this one particular dress that Mildred wears so much—her “good dress.” The whole thing is painstakingly and beautifully shot—there’s a lot of pale green in it that has now been seared into my brain. I was mesmerized. HBO means “Hi, basically outstanding.” —Sonja

Dogtown and Z-Boys (2001)
I have terrible balance and wilt instantly in direct sunlight, but watching this excellent documentary about teenage skateboarders in Venice, California, in the 1980s makes me feel like I could do a kickflip and get a suntan at the same time. The Z-Boys, or the Zephyr team, were the coolest kids in the coolest town, which basically made them the coolest people in the world. Of course, with any surge of fame comes a dizzying fall, and no one knows that more than a skateboarder. When you finish watching this movie and are still hungry for more (which you will be), you can take solace in The Lords of Dogtown, a feature film that dramatizes the Z-Boys’ story, co-starring Heath Ledger. What more could you ask for, really? —Emma S.

Mulholland Drive (2001)
Here are two facts about the Mulholland Drive DVD: 1. Director David Lynch believed that not watching the movie in one sitting would ruin the mood he was trying to create, and so scene selection does not exist for the two-and-a-half-hour film. 2. The DVD comes with a list of 10 clues to “unlock the thriller,” with cryptic hints including “notice the appearances of the red lampshade” and “an accident is a terrible event…notice the location of the accident.” This should give you an idea of what to expect from his surrealist noir thriller. I would say it’s best to not know much else before watching it. This was the first work by Lynch that I ever watched—before Twin Peaks, before Blue Velvet, before Eraserhead—and I didn’t know anything about him beforehand. I remember sitting alone in my basement after the end credits rolled, thinking, What the hell was THAT. I promptly sought out the rest of his movies. —Anna

L.A. Story (1991)
Steve Martin wrote and starred in this ode to the beauty and absurdity of Los Angeles. He plays Harris K. Telemacher, a wacky weatherman who happens upon a magical freeway signpost that helps him find love. One of the women he meets is gum-chewing salesgirl SanDeE* (yes, that’s how she spells her name), played by Sarah Jessica Parker, who twirls constantly, wears a fanny pack, and is the embodiment of breezy California-girl spirit. The whole movie is hilariously surreal (crosswalk signals flash “uh like walk” and “uh like don’t walk”) and sprinkled with so many wonderful lines (“I was deeply unhappy, but I didn’t know it because I was so happy all the time” and “a kiss may not be the truth but it is what we wish were true”). —Amber

Nowhere (1997)
If you like fucked-up art films about sex-crazed teenagers, you will totally love Gregg Araki’s Nowhere! The only problem is, it’s not available on DVD in the US (where I am) but hopefully it will be coming soon—and meanwhile, a little commenter bird told me that the whole thing is on YouTube, yippee! The movie is about a group of teenagers living in Los Angeles, the protagonist being Dark Smith, an aspiring filmmaker who is struggling with his sexuality. The movie follows Smith, his girlfriend, and their circle of friends as they party the day away (encountering aliens, playing X-fueled hide-and-go-seek, etc.) in the wake of an apparent apocalypse. It’s super trippy, funny, and dark. It is also so weird that it’s hard to explain; you just have to SEE it. —Hazel

Somewhere (2010)
Sofia Coppola’s Somewhere is a good movie aesthetically, not so much storywise—it’s not very exciting. But its quietness makes it really beautiful to watch. It follows Cleo (the eternally adorable Elle Fanning), the daughter of a movie star (Stephen Dorff) who is stuck in a sort of midlife crisis, and examines their changing relationship. It takes place in Hollywood, mostly at the Chateau Marmont, as the pair lounge by the pool, order gelato, and play Guitar Hero—and along the way learn to challenge their old ideas of family, success, and fame. —Hazel

Gas Food Lodging (1992)
This movie is a love letter to mothers and (fatherless) daughters. It has it all: an amazing cast (Fairuza Balk, Ione Skye, Brooke Adams), beautiful scenery with that really good light like in Robert Altman’s Three Women, ace teenage-bedroom décor, heartbreak, Donovan Leitch wearing tons of makeup, “Magic” by Olivia Newton-John, phosphorescence, silver hot pants (really nice vintage clothing overall), tumbleweeds, a slut-shaming comeuppance scene, and a cameo by J. Mascis (who composed most of the soundtrack). Best quote: “Women are lonely in the ’90s. It’s our new phase. We’ll live.” —Sonja
P.S. For the life of me, will someone PLEASE tell me what the awesome song is that’s playing in the background of this scene?

All About Eve (1950)
Bette Davis plays Margo Channing, a talented actress who is considered “old” (i.e., 40). Eve, played by Anne Baxter, is an obsessed fan who becomes Margo’s assistant. However, Margo soon begins to suspect that Eve is using her role as assistant to launch her own acting career. The film raises some good points about how female worth tends to be closely associated with youth, and how women are both subtly and overtly positioned to be in constant competition with each other. What I love most about it is its script, filled with rapid-fire jokes and one-liners delivered expertly by Davis. There is also a cameo by a younger Marilyn Monroe, who is always fun to watch onscreen. —Anna

Martha Marcy May Marlene (2011)
After seeing this movie, I can’t look at idyllic white farmhouses in the New York countryside without getting chills. Martha (Elizabeth Olsen) plays a free-spirited ingénue who left her family to live in the Catskills with a dysfunctional neo-hippie cult led by Patrick (John Hawkes), a charismatic and abusive leader. In addition to changing Martha’s name to “Marcy May,” Patrick systematically integrates her and a bevy of other vulnerable souls into a web of deceit, drugs, violence, theft, rape, and mind control. Triggered by harrowing events within the cult, Martha flees the commune and returns to the only real family she has left—her sister, who lives in a big house in Connecticut with her husband. There, Martha struggles with getting used to life beyond the cult. It’s not easy! The storyline allows us to travel through Martha’s distorted and paranoid memories as she fights to relocate her sense of self, time, voice, and freedom. I don’t recommend watching this movie at night like I did, or you might have nightmares of John Hawkes whispering “let us in” super creepily. —Jamia ♦