Woody Allen movies don't make for quite as apples to apples comparisons as Bertie and Jeeves  novels or Aubrey and Maturin novels , since some are intentionally serious and unappealing. But they are still worth plotting out inflation-adjusted domestic box office over time (data from BoxOfficeMojo ).
The Gross column is in millions of today's dollars. The Versus Mean column compares box office to Woody's mean box office (a little under $30 million current dollars). Thus, Annie Hall's $133 million in today' dollars is 350% more than (or 4.5 times) his $30 million mean.
|Everything You Always …||1972||36||82||178||4|
|Love and Death||1975||39||76||157||6|
|A Midsummer Night's Sex Comedy||1982||46||24||(19)||18|
|Broadway Danny Rose||1984||48||25||(17)||17|
|The Purple Rose of Cairo||1985||49||23||(22)||19|
|Hannah and Her Sisters||1986||50||84||181||3|
|Crimes and Misdemeanors||1989||53||36||21||8|
|Shadows and Fog||1992||56||5||(83)||33|
|Husbands and Wives||1992||56||20||(33)||21|
|Manhattan Murder Mystery||1993||57||21||(28)||20|
|Bullets Over Broadway||1994||58||25||(16)||16|
|Everyone Says I Love You||1996||60||17||(44)||24|
|Sweet and Lowdown||1999||63||6||(79)||31|
|Small Time Crooks||2000||64||25||(16)||15|
|The Curse of the Jade Scorpion||2001||65||10||(65)||28|
|Melinda and Melinda||2005||69||5||(84)||34|
|Vicky Cristina Barcelona||2008||72||25||(15)||14|
|You Will Meet a Tall Dark Stranger||2010||74||3||(89)||36|
|Midnight in Paris||2011||75||55||86||7|
|To Rome with Love||2012||76||17||(44)||23|
We are missing box office data for his early comedies like Take the Money and Run.
Before those, he was a joke-writing prodigy making thousands of dollars per week as a teenager in the mid-1950s. It took him longer to develop as a stand-up comic, then as a movie star and director, getting started in movies just before turning 30.
His comedies in the first half of the 1970s like Sleeper did consistently well, then he peaked with Annie Hall and Manhattan in the late 1970s when he was in his early 40s.
True fact: as originally filmed, Annie Hall was a two hour and 20 minute murder mystery. Allen's editor, Ralph Rosenblum, convinced him to dump the entire crime plot (which was resurrected years later in Manhattan Murder Mystery), add some voice-over, and voila, he had a short romantic comedy. Although Annie Hall won the Oscar for Best Picture, Rosenblum wasn't even nominated for Best Editing. (Granted, Star Wars won, and deserved to win, Best Editing, but still ...)
Hannah and Her Sisters in 1986 was a big peak, followed by Crimes and Misdemeanors in 1991. Then he made 21 straight movies that failed to reach his mean, which has to be some kind of record.
My impression is that Allen doesn't run over budget, so his financial backers know that although they will probably lose money, their losses will be limited. So, they are more patrons than investors, but they also have a chance of making a profit. So, funding a Woody Allen movie is like buying a ticket in a charity raffle. And, Allen's prestige and popularity with Oscar voters means that big movie stars will work in his films cheap, so his patrons get extra vicarious glamor from dropping a quite finite amount of money on his projects.
And then, just when it seemed completely hopeless, at age 75 he made 2011's very entertaining Midnight in Paris.