2000-2010: Stop Me If You’ve Heard This One Before...

A summary at the movies Woody Allen made from 2000 to 2010

Woody Allen

Trevor Gilks


After 35 years of making movies, Woody Allen finally hit a sustained dry patch at the beginning of the new century. His support from audiences had been dwindling since the late 1980s, but now critics, journalists, and even his loyal fans had begun to turn on him. Most people, including myself, just didn’t think his new movies were as good as they used to be.

In the first half of the decade, Allen’s career appeared to be in free-fall. 2000’s Small Time Crooks was well received, although it was a notable step-down from the tighter, more ambitious movies Allen made in the late 1990s. Following that, he made four films that were widely panned by critics and considered financial bombs.

His movies frequently ripped off material from his older work, and several had been written or conceived decades earlier. The worst part was that they felt rushed, sloppy and indifferent, as if he was just going through the motions.

In the second half of the decade, things took a turn for the better. In 2005, just when it seemed like he might not even be able to get the money together for a new movie, he made Match Point, an Oscar-nominated international hit. It was not a sustained comeback, though — while 2008’s Vicky Cristina Barcelona was an even bigger hit, Allen’s other four movies in the second half of the decade got the same indifferent reception as those in the first half.

All that said, Allen made only one film that was truly terrible, and while he did not demonstrate much enthusiasm for originality, the better films of the decade contained traces of the wit and intelligence that made him famous. Movies like Scoop and Whatever Works were reminders of how effortlessly funny Allen can be. Match Point revisited the dark psyche that made movies like The Purple Rose of Cairo and Crimes and Misdemeanors so interesting, and Vicky Cristina Barcelona had the same unmistakable ear for dialogue and characters that once made Woody Allen one of the world’s most beloved filmmakers.

Who Was Woody Allen in 2010?

Woody Allen veered back and forth from comedy to drama more than ever before, but what his movies had in common was that they were all, excepting The Curse of the Jade Scorpion, straightforward comedies or literal human stories. The narrative gimmicks and genre-blurring flourishes of the past were gone. Woody Allen was once a boldly inventive and audacious filmmaker, but now he was playing it safe.

He started to gain a reputation as a lazy director who filmed everything in one take and rarely provided his actors with direction. Reviews constantly bemoaned his prolific output, suggesting he cease to stubbornly make a movie every single year.

Yet, despite all the poor press, Allen’s public persona made a dramatic positive shift. Once incredibly reclusive, Allen now started to appear at festivals, pose for pictures in magazines, and doing extensive promotional press interviews after decades of being mostly silent. He even appeared at the Academy Awards. While the rest of the world thought Allen’s movies were declining in quality, he disagreed, claiming Match Point, Hollywood Ending, Anything Else and even Cassandra’s Dream to be among his best movies. Woody Allen may not have had anything new to say, but he was having fun saying it anyway.

2000-2010: 5 Favorite Performances

  1. Penelope Cruz, Vicky Cristina Barcelona
    Penelope Cruz in Vicky Cristina Barcelona

    So many of the characters in Allen’s ‘00s movies were personality-deprived clones, but Maria Elena was a true original. As a hilariously temperamental Spanish diva, Penelope Cruz was funny, intense, and eminently watchable.

  2. Javier Bardem, Vicky Cristina Barcelona
    Javier Bardem in Vicky Cristina Barcelona

    It is a testament to his acting skill that Javier Bardem was able to seem so convincingly morose about spending Vicky Cristina Barcelona holding the fates of three beautiful women in his hands. Bardem was graceful yet tormented and capable of making even the simplest lines seem like deep, romantic truths.

  3. Larry David, Whatever Works
    Larry David in Whatever Works

    Larry David was the only performer in the 2000s, other than Allen himself, to have an entire Woody Allen comedy build around his performance. Boris Yelnekoff was not a man everybody liked, but he was the best and most consistently written character outside of Match Point or Vicky Cristina Barcelona. The character could easily have emerged as sour and unpleasant, but David was able to make him lovably grouchy.

  4. Tracey Ullman, Small Time Crooks
    Tracey Ullman in Small Time Crooks

    Tracey Ullman served as the emotional core of Small Time Crooks, a movie that otherwise flailed about in all directions looking for meaning and laughs. Ullman absorbed the movie’s twists and turns in stride, and managed to offer a warm, grounded presence that put a human face on the movie.

  5. Jonathan Rhys Meyers, Match Point
    Jonathan Rhys Meyers in Match Point

    Woody Allen reportedly directed Meyers in Match Point by saying, “80% of the work was already done when you woke up in the morning.” While it’s true that Meyers’ icy pout and stand-offish demeanor have a lot to with his characterization of Chris, Allen is perhaps slightly underestimating Meyers. Chris is deceptively chameleonic, behaving differently depending on his company, and it’s thanks to Meyers’ emotional control and deliberate mysteriousness that he’s equally convincing in all his incarnations.

2000-2010: 5 Favorite Movies

  1. Vicky Cristina Barcelona
    With Vicky Cristina Barcelona, Woody Allen does what every director should do: he makes it seem very easy. VCB has an effortless, breezy grace, and a story that unravels naturally but unexpectedly. Every one of the movie’s primary characters are interesting and vividly realized.
  2. Match Point
    Match Point was a towering achievement amidst the movies of the ‘00s — an effortful, intelligent movie, and one that was as suspenseful and exciting as anything Allen had made in decades. For any other director, Match Point would be an impressive showcase — for Allen, it is a reminder of the mastery he once had over his art-form.
  3. Whatever Works
    There was a time when Woody Allen’s comedies were so smart and well-crafted that they stood alone as works of art beyond their jokes and gags, but that’s not really the case anymore. Whatever Works, Scoop, Anything Else and Hollywood Ending are all dated, recycled comedies with shallow characters and stories that don’t hold up against even the slightest examination. The only differentiation is how funny you happen to find the jokes. Personally, I laughed the most during Whatever Works, thanks mostly to Larry David’s sardonic performance and dialogue, although the same might not be true of you.
  4. Melinda and Melinda
    In a decade of movies that pillaged and borrowed from Allen’s past, none did so as pervasively as Melinda and Melinda. There isn’t a shred of originality, but it’s executed with a light touch and a surprisingly sharp sense of humor.
  5. Small Time Crooks
    Discussing Woody Allen’s 2000s movies often comes down to a game of fractions. Melinda and Melinda breaks down into halves, and Small Time Crooks is made up of three distinct thirds — one hilarious, one toxic, and one that’s somewhere in between. The movie begins with a promising return to Allen’s unburdened slapstick heyday, but then devolves into a poorly realized social satire and what seems like 30 minutes of wheel-spinning. Woody Allen’s central performance can be grating, but the supporting cast — especially Elaine May, Jon Lovitz and Tracey Ullman — are all pretty funny.