To be funny with the camera is a tricky thing. Comedy generally lies in the writing & the performances, but to "direct funny" seems like an abstract thing. Though, once upon a time, Woody was able to do that to some degree - actually using the frame to tell jokes beyond the physicality & the dialogue. But, alas, his strengths never really lied in his directing abilities (with the exception of Interiors), so we'll just say it's "okay" that my favorite Woody movie is Play it Again, Sam, even though the title of director goes to Herbert Ross.
The film is based upon Woody's play of the same name. So, for a guy who's made a film nearly every year for nearly forty years, one gets the sense of nurture with this film; he spent more time with this story & this character than any of the stories or characters that followed. & while most may argue that all those stories & characters are pretty similar to one another, I personally draw a straight line from this movie to Annie Hall - the one most consider to be his masterpiece. I've always found Annie Hall to be Play it Again-Lite - the slightly intellectualized version. Not that it's nearly as silly as Bananas or Love & Death -- for me, Play it Again has always been the perfect balance - right where he needed to be. A+