1. 1.
    Match Point
    An unpopular opinion, BUT I think this movie is perfect. It's a perfect film. There is no fat. Ferris Bueller's Day Off, Jaws, and Match Point are three examples of perfect movies. If you ever need to commit a murder, use Match Point as a reference. Highlights include: every second of this film, poor Mrs. Eastby, the tennis ball/jewelry call back, and the beginning, end, and middle of this movie.
  2. 2.
    Stardust Memories
    Near perfect. It's beautiful and hilarious. Allen denies that it's a self reflexive piece. If you subscribe to the "author is dead" theory then fine, but if you don't, of course it's about Allen. Highlights include: Charlotte Rampling, Tony Roberts, Daniel Stern and gorgeous cinematography by Gordon Willis.
  3. 3.
    Hannah and Her Sisters
    My favorite Dianne Wiest performance of all time. Love her as the black sheep sister. Highlights include: Michael Caine, Max Von Sydow, Daniel Stern, and cinematography by Carlo Di Palma.
  4. 4.
    Crimes and Misdemeanors
    Tons of laughs and super dark. Anything to do with seemingly REAL people involved in murder is terrific. Highlights include: Anjelica Huston, Martin Landau's face, and every single line from Alan Alda.
  5. 5.
    Husbands and Wives
    Incredible performances from Judy Davis, Sydney Pollack, and Mia Farrow. There's a great scene where Lysette Anthony's character throws a tantrum at a party trying to embarrass Sydney Pollack for being a complete asshole. Worth it just for that scene. Highlights include: Liam Neeson before he was Taken.
  6. 6.
    Far and away the most beautiful of Allen's movies. Batshit crazy beautiful cinematography by Gordon Willis. I watch the opening New York montage every morning with coffee. Highlights include: every frame of this movie, the shot of Allen's apartment at night with the spiral staircase lit up. And the every piece of chosen music in the film.
  7. 7.
    Annie Hall
    Much of the film that we've come to know and love came together in the editing room. A whole major plot of the film was cut out and recycled in Manhattan Murder Mystery. Highlights include: Diane Keaton everything, Tony Roberts' lifestyle, young Christopher Walken, sleazy Paul Simon, and a brief moment with John Glover.
  8. 8.
    Sweet and Lowdown
    I'm a huge fan of Gypsy Jazz music and all things Django Reinhardt. Highlights include: Sean Penn comedy/Sean Penn shooting rats by a dumpster.
  9. 9.
    Deconstructing Harry
    This film is sort of comprised of a series of vignettes. The plot pops in and out of "reality", jumping into Allen's character's novel. Highlights include: Judy Davis pulling a gun on Allen, Billy Crystal as the Devil, Tobey Maguire losing his virginity to a call girl and then meeting the Grim Reaper, and a very funny performance from Robin Williams as a literally out of focus actor.
  10. 10.
    Midnight in Paris
    If you love Gypsy Jazz and Paris and magic and time travel and beautiful people... this film is pretty damn perfect. Highlights include: "Bistro Fada" by Stephane Wrembel, pedantic Michael Sheen, Owen Wilson's every beat, uh, and um, Allison Pill as Zelda Fitzgerald, and most importantly, Corey Stoll as Hemingway.
  11. 11.
    Everything You Always Wanted to Know About Sex *But Were Afraid to Ask
    This one is made up of a series of shorts all centered around sex. All are great. But I have never laughed harder watching a movie than I did during the Gene Wilder short. Highlights include: laughing extremely hard at Gene Wilder for like, an hour. The kind of laughing that scares you because you can't breathe and maybe it's forever. Also, Woody Allen dressed as sperm.
  12. 12.
    The Purple Rose of Cairo
    One of my favorite plots of pretty much any film. The original Last Action Hero. Highlights include: double Jeff Daniels and depression era sets and wardrobe.
  13. 13.
    Bullets Over Broadway
    A terrific period piece film. Everything from the script to the cast to the music works so well in this movie. Highlights include: John Cusack, Jennifer Tilly, Chazz Palminteri as a mob bodyguard with a knack for playwriting, and Carlo Di Palma cinematography.
  14. 14.
    Mighty Aphrodite
    This movie came out in 1995 when I started to become a Woody Allen fan. It holds a dear spot in my heart. Highlights include: a heart of gold prostitute played by Mira Sorvino, a hilariously dim bulb played by Michael Rapaport, and a Greek chorus lead by F. Murray Abraham.
  15. 15.
    Broadway Danny Rose
    Mia Farrow for once playing against type in this terrific Woody joint. Highlights include: Nick Apollo Forte and cinematography by Gordon Willis.
  16. 16.
    Woody Allen denies that he was heavily influenced by Ingmar Bergman in making this film. I mean... he was though. For sure. Obviously. There is perhaps not one moment of levity in Interiors. But it's wonderfully directed. Highlights include: a beautiful single take tracking shot of two characters walking along the beach.
  17. 17.
    Woody Allen being very Marx Brothery. Highlights include Allen trying to buy pornography, a young Sly Stallone, and Woody's character name 'Fielding Mellish'.
  18. 18.
    Radio Days
    Great sets and clothing and music and laughs. One of the most rewatchable of Allen's movies. Highlights include: a very young Seth Green, a very funny scene with Danny Aiello ditching Dianne Wiest, and all things Wallace Shawn.
  19. 19.
    Love and Death
    There are so many incredible jokes in this movie. It's nonstop chaos. Highlights include: for every joke there is another joke. This movie goes joke per joke. Also, James Tolkan with hair.
  20. 20.
    Heavy Marx Brothers future antics. A favorite as a child even though I understood none of it. Highlights include: The Orgasmatron, which I still barely understand.
  21. 21.
    Another unpopular opinion to rank Celebrity so high. But Kenneth Branagh is my favorite Woody Allen proxy. I think Ebert wrote that Branagh's version of Allen is basically just an incredible impression of Allen, so why not just have Allen play the part. I get that, but it's so much fun to watch Branagh trip his way through this film. Highlights include: Leonardo Dicaprio with his entourage of David Blaine, Tobey Maguire, and Entourage's Adrien Grenier.
  22. 22.
    Shadows and Fog
    Another story about murder! Highlights include: murder! beautiful black and white cinematography by Gordon Willis, John Malkovich as a clown, and Madonna.
  23. 23.
    I love Spinal Tap and I love Christopher Guest movies, but Zelig is the greatest mock-documentary ever made. It's so well put together and seemingly real. This will be the first Woody Allen film my children will see. I want them to think its real for a few years.
  24. 24.
    Everyone Says I Love You
    I'm usually not a fan of movie musicals unless they're called Grease or Mary Poppins, but this film is pretty special. Almost nobody in the cast is a trained singer/dancer which makes it all feel a little more accessible. Highlights include: Edward Norton singing and dancing. And a Billy Crudup duet with a cabbie.
  25. 25.
    Manhattan Murder Mystery
    The recycled murder plot from Annie Hall. It's great to see Diane Keaton and Woody as a couple again and Alan Alda getting in between them. Highlights include: favorite restaurant oner from any Woody film, and cinematography by Carlo Di Palma
  26. 26.
    Vicky Cristina Barcelona
    Part of Allen's travel series. Highlights include: beautiful cinematography, great music (including a track by Midnight in Paris collaborator Stephane Wrembel), Javier Bardem and Penelope Cruz screaming at each other in Spanish, and most importantly, Chris Messina.
  27. 27.
    A Midsummer Night's Sex Comedy
    Love the early 20th century setting. Highlights include: Woody's character's inventions and Julie Hagerty.
  28. 28.
    Small Time Crooks
    Not particularly great, but holds a dear spot in my heart. Highlights include: Jon Lovitz everything, Michael Rapaport, and Hugh Grant. Also, want Hugh Grant in 100% more Woody Allen films.
  29. 29.
    Don't Drink the Water
    The second film version of Woody Allen's 1966 play. Highlights include: Michael J. Fox and every single thing Dom DeLuise does in this film. Also, cinematography by Carlo Di Palma.
  30. 30.
    Blue Jasmine
    Cate Blanchett is incredible here, but I wish the film was as great Blanchett's performance. The supporting cast is also pretty terrific, namely Bobby Cannavale and Sally Hawkins. Highlights include: oh my god Andrew Dice Clay is in this.
  31. 31.
    Another Woman
    Also influenced by Bergman. Highlights include: Gene Hackman. God, I miss Gene Hackman.
  32. 32.
    Cassandra's Dream
    Not a particularly great film, but again, love the murder plot and unusual Allen cast of Ewan McGregor and Colin Farrell. Highlights include: Tom Wilkinson and a tense score by Philip Glass
  33. 33.
    Take the Money and Run
    A mockumentary about a thief. It has several very funny moments, but it's too disjointed to find it as relaxing as his other films. Highlights include: Interviews with Woody's parents disguised in Groucho glasses so as to disguise their identity.
  34. 34.
    Melinda and Melinda
    A great idea from Woody. One story told two ways. As a comedy and as a tragedy. The film's quality, however, doesn't quite meet that seemingly interesting idea. Highlights include: Chiwetel Ejiofor everything and Wallace Shawn as basically his character from My Dinner With Andre.
  35. 35.
    Mia Farrow back to playing Mia Farrow. Allen shot this film twice after deciding it wasn't working with the original cast. Highlights include: Elaine Stritch and Sam Waterston.
  36. 36.
    What's Up, Tiger Lily
    Sort of Woody Allen's first film. He recut and dubbed scenes from a Japanese film and spliced in original scenes to create a new plot around an egg salad recipe. Love the idea, though the film is perhaps a little dated at this point.
  37. 37.
    I don't really enjoy the magical realism aspect of this movie. I wish there was just a grounded Woody Allen film starring William Hurt. Highlights include: cinematography by Carlo Di Palma
  38. 38.
    The Curse of the Jade Scorpion
    I want to like this movie. Every time I watch I want to like it. I love that it's about magic and I love the 1940s setting, but it never fully works. Highlights include: Allen as a private eye. And Helen Hunt. I wish she were in more Woody films.
  39. 39.
    You Will Meet a Tall Dark Stranger
    Love Anthony Hopkins in this film. Also, worth it for the Josh Brolin subplot about stealing another writer's manuscript. I wish the film were as grim as the title. Highlights include: Josh Brolin's curly hair.
  40. 40.
    Magic in the Moonlight
    Pretty forgettable movie. Nothing here is particularly compelling. I maybe fell asleep in the theatre. Highlights include: Emma Stone and Colin Firth being so damn likable, and the really comfy seats at the Arclight.
  41. 41.
    Hollywood Ending
    This one has some decently funny moments. I like Allen's physical work. I just think the casting ruined this film. Tea Leoni is particularly bad. And what do people really think about Treat Williams?? He's no Tom Berenger. Highlights include: Allen's physical comedy for maybe the last time.
  42. 42.
    Whatever Works
    Probably the biggest film disappointment for me next to the Matrix sequels. This was supposed to be the confluence of comic genius. It was not. But it brought Woody back to New York for a minute. Highlights include: NYC, Henry Cavill pre superman, Michael McKean, and Ed Begley Jr.
  43. 43.
    Anything Else
    Eesh. None of the dialogue sounds right coming out of Jason Biggs' mouth. He can't be to blame though. He isn't as horrible as people say, he just isn't... very good. At all. Highlights include: Jimmy Fallon.
  44. 44.
    Ahh, Scoop, Scoop, Scoop. Even with a murder plot, almost especially with a murder plot, I hate you Scoop. Highlights include: Woody Allen back on screen and Ian McShane delivering lines by Woody Allen.
  45. 45.
    To Rome With Love
    At least Scoop has a plot I guess. I don't even remember what this movie is about. I think this the only Woody Allen movie I have seen one time. None of these overlapping stories mesh. Highlights include: Woody and Judy Davis playing a couple.