Few filmmakers have ever left a mark on American pop culture as big as John Hughes did. He parlayed an ad copywriter job into a writing gig at The National Lampoon, parlayed that into a screenwriting career, and then basically reinvented the teen comedy. He was extremely prolific in the 1980s (legend has it he wrote Sixteen Candles over a weekend), and between 1983 and 1987 he produced a classic every single year, including Pretty In Pink and Ferris Bueller’s Day Off in 1986 alone. Then, hoping to broaden his comedy horizons, he hooked up with John Candy and proved he could make hits for adults, too. By 1990 his legacy was secure, but he didn’t stop there. He moved on and made one of the most successful family comedies in history: Home Alone.

Though the legend of John Hughes will always come back to the teen films, his career is a fascinating mix of influences and interests. There are the films everyone remembers, and then there are the surprisingly effective Disney remakes, and the indie movies, and even a weird pirate adventure. This month, because Hughes’ classic Vacation is getting the reboot treatment, I decided to look back at it all and try to lay out the best and the worst. So, here’s every John Hughes movie, ranked.

A NOTE ON THE RULES OF THIS LIST: We decided that this would be a list of “John Hughes Movies,” and defined that as any film he put his name on, either as a writer, a director, or a producer. Because he elected to use a pseudonym on a few films, like Beethoven, we decided that those films did not qualify as “John Hughes Movies,” and left them out.

31. NEW PORT SOUTH (2001)
This indie drama was written by Hughes’ son James, and is one of only two films on which he acted as only a producer. It’s really a shame this is the last film to bear his name. It’s well-intentioned, but ultimately too self-serious and grating. By the end it almost feels like a parody of a Hughes flick, and not in a good way.

30. REACH THE ROCK (1998)
As his career was winding down, Hughes wrote and produced this little movie about a guy who can’t let go of his past, and aside from a few moments of cleverness, it just feels like a bland and ineffective rehash of themes he already explored in better movies. It’s so forgettable that it turns out to be the only Hughes flick you still have to watch on VHS.

29. NATE AND HAYES (1983)
You’d really think a Tommy Lee Jones-led pirate adventure from the ‘80s would be more fun than this.

28. JUST VISITING (2001)
Hughes’ last screenplay credit (under his real name) is this weird remake of a French film about a knight transported to modern times. Listen, I’ll watch Jean Reno in anything, but watching him guzzle Chanel No. 5 and scream every time he rides in a car gets old pretty fast.

Hughes’ first screenplay was this attempt to replicate the success National Lampoon had with Animal House. It didn’t work, but there’s just enough horror-comedy weirdness to make it worth checking out, if only as a kind of relic of the times.

26. BABY’S DAY OUT (1994)
There’s a moment or two of charm, but this is easily the weakest of Hughes’ “Hapless Crooks Outwitted by a Child” films. Home Alone, but with a baby, isn’t as fun as you might think.

The kids get grating after a while, and the physical comedy isn’t as clever or charming as it is in better efforts like Home Alone, but Walter Matthau as Mr. Wilson is perfect casting.

24. CURLY SUE (1991)
Hughes’ final film as a director has its heart in the right place, but the problem is there’s just not enough heart there. Jim Belushi can do Lovable Scoundrel, but not as well as John Candy or Ed O'Neill.

John Candy and Dan Aykroyd have to work so very hard for every laugh they get in this movie, and they still don’t end up getting many.

22. FLUBBER (1997)
Robin Williams was very good at carrying movies, and he brings some real heart and energy to what could’ve otherwise just been Home Alone with dancing, CGI green goo.

21. HOME ALONE 3 (1997)
The odds were completely against this movie being any good at all — with a new cast, a new premise, and a new set of crooks — but the film wrings every bit of enjoyment possible out of a plot that’s an even bigger stretch than Home Alone 2 and a series of physical gags that should’ve killed the crooks the moment they walked in the front door.

20. DUTCH (1991)
Dutch is a kind of weird hybrid of Uncle Buck and Planes, Trains, and Automobiles if you were to swap Steve Martin out for an absolutely horrible kid. It’s not as good as either of those films, but Ed O'Neill still makes it sort of work.

There are so many moments when this movie seems like it can’t figure out what it wants to be, and it ends up disjointed and meandering. On the bright side, there are some laughs, and if you didn’t get a crush on Jennifer Connelly while watching The Rocketeer, you will definitely develop one here.

18. 101 DALMATIANS (1996)
Glenn Close is flawless in every scenery-chewing moment as Cruella de Vil, and though much of the movie kind of evolves into “Home Alone with puppies,” she makes the whole experience worth it.

The premise is much flimsier than the first one, and the gags become so cruel that this movie gets harder to watch the older you get, but there’s still enough charm and heart to make it worth watching. There’s also Tim Curry, which I think makes any movie worth watching.

Many of the gags feel like a rehash of the original Vacation, but Hughes had hit his stride at this point, and he knew how to write the Griswolds, so there’s still plenty of fun to be had.

15. SHE’S HAVING A BABY (1988)
Hughes’ effort to move into a more serious look at adulthood never works quite as well as you want it to, but all those cozy character charms that made stuff like Pretty In Pink work still brighten things up considerably.

14. ONLY THE LONELY (1991)
Hughes is only the producer here, lending his name to a Chris Columbus film that, while predictable, can win you over thanks a terrific cast and great performances by John Candy and Ally Sheedy.

This movie has absolutely no right to be as enjoyable as it is, but it’s about as good as a remake of a universally accepted classic could be. Lord Richard Attenborough as Santa doesn’t hurt, either.

12. WEIRD SCIENCE (1985)
The very premise is somewhat grating to my 2015 mind, but weird sexist stuff aside, Hughes’ attempt to take his knack for teen comedy into the realm of sci-fi is actually still a lot of fun.

11. HOME ALONE (1990)
You can knock it as a cynical exercise in commercial filmmaking all you want, but this movie just works. It’s got laughs, it’s got heart, and it’s got John Candy as the Polka King of the Midwest.

10. MR. MOM (1983)
All the jokes feel predictable now, and some of them feel flat-out dated, but Michael Keaton’s terrific timing still holds this movie together 32 years later.

Hughes’ last true teen comedy is also one of his most interesting films. It’s kind of a reverse, slightly more mature Pretty In Pink, with an added dose of teens who are really starting to grapple with their futures. If Sixteen Candles is freshman year for Hughes, this is graduation.

I am perfectly willing to admit that my childhood fondness for this film (and my Christmas superfandom) may mean I’m placing this too high on the list, but I don’t care. I’ve seen this movie more than almost any other on this list, and every time it gets me. Hughes knew exactly how to work the dynamics of these characters, and for his last time out with the Griswolds (he had no involvement in Vegas Vacation) he brought more heart than either of the other two movies combined. It’s genuinely moving, and you also get to watch Randy Quaid dump liquid poop into a storm drain. What more could you ask for?

7. PRETTY IN PINK (1986)
It’s not as clever as Sixteen Candles, and it doesn’t have the depth of The Breakfast Club, but Hughes nails so much about the teen experience here that — record stores and fashion choices aside — it doesn’t feel like a dated movie. You could make this today and it would still be great.

The first voyage of the Family Griswold doesn’t work because the gags are so big and broad or because the supporting cast is so wacky, though that’s all great. It works because, as with so many of his films, Hughes started with a well-defined group of characters who had a well-defined family dynamic, then picked them apart through the circumstances of the trip. It’s built on such a simple idea, but the attention to detail is what makes it great.

It’s more fueled by spectacle and cynicism than Hughes’ other teen comedies (well, except perhaps Weird Science), but you can’t deny that it works, implausible as the whole premise seems. Hughes had a knack for building teen characters into believable people who could also seem like gods, and that means when Ferris climbs up on that parade float, you’re not just watching him. You are him.

I hate myself a little for ever having laughed at “Long Duck Dong,” but that aside, this is a teen comedy masterpiece. Hughes had never attempted a film like this before in his career, but somehow he instinctively found the perfect balance between slapstick and character that makes this such a landmark movie. He also found Molly Ringwald, which didn’t hurt.

Hughes’ transition from teen comedies directly into a film like this is improbably flawless. That’s thanks in part to Steve Martin and John Candy, who are perfect together, but also to the careful layering in of the film’s emotional core. It’s a movie about how we find people to love in unlikely places, something Hughes did in his teen films, but this time it’s about a love between two men, and Hughes approaches that part of the film without cynicism or fear. There’s something really beautiful about it.

2. UNCLE BUCK (1989)
An essential John Candy performance, and an essential '80s comedy. Hughes played over and over again with the trope of a nice guy falling all over himself in an unlikely situation (Mr. Mom, Dutch, and so on), but here he nailed it. Home Alone made the most money, but Uncle Buck is the perfect family comedy in the Hughes filmography.

I know, it’s a predictable answer, and it might even be an easy answer, but it’s the right one. The Breakfast Club doesn’t quite make sense in the overall landscape of '80s teen comedies, to the point that I don’t know if anyone but Hughes would’ve had the clout to make it at the time. Almost all of it takes place in a single room, nearly every joke is verbal, no one goes to a party or crashes a car or gets ready for the big dance, there are no sex scenes, it’s R-rated with no nudity, and the third act is about talking out serious issues, not laughs. Hughes knew what he was doing, though, and the film wound up being a masterclass in telling stories about teenagers, and in constructing character arcs. When those five kids walk into that library, they are unquestionably archetypes, right down to Claire getting detention for skipping school to go shopping. Slowly, methodically, and flawlessly, Hughes spends the rest of the movie unspooling everything we think we know about them, and everything they think they know about each other. By the end, they’re The Breakfast Club, and we’re pumping our fists to Simple Minds. It’s a masterpiece.