“Deconstructing Harry” (1997)
One of Allen’s most uncompromised, angriest works, “Deconstructing Harry” is also, with distance, one of his strongest. Allen plays Harry Block, a tortured writer who is undergoing a breakdown in his twilight years, as fantasy and reality begin to merge. While he has used his friends and family for inspiration frequently, his works start to come to life and intermingle with his own, throwing him into a tailspin as he deals with the side affair of another lover and a career honor he feels is undeserved. The film is one of Allen’s most autocritical works, taking to task both his critics and his own artistic/masturbatory tendencies, but it’s also filled with a number of absurdist touches provided by a peculiar all-star cast -- look out for Billy Crystal in a memorable cameo as The Devil. “Deconstructing Harry” has moments of free-form hilarity, but the self-serving pettiness of his characters are also refreshingly on display, painting a portrait of an artist in transit who can never sit still, even as his work begins to cannibalize him. [B+]

“Celebrity” (1998)
Of all the Woody Allen surrogates throughout the years (Owen Wilson being the most recent), none are weirder than Kenneth Branagh as a novelist-turned-tabloid journalist (following, of course, a disastrous divorce) in "Celebrity." The casting of the British thespian is bizarre in and of itself, especially since "Celebrity" was released at the tail end of Branagh's impressive Shakespeare run. But what's even odder is how spot on Branagh is in terms of mimicking Allen's series of jerks, tics and stutters. It's uncanny and spot-on in ways that few of the Allen stand-ins usually are, and it makes "Celebrity," which is basically a series of vignettes with Branagh bumping into various celebrities (usually playing exaggerated versions of themselves), way more compelling. The best cameo goes to Leonardo DiCaprio, upending his badboy image by snarling that Branagh is so sensitive that he "should write fucking greeting cards." [B]

“Sweet and Lowdown” (1999)
Though Woody Allen’s has often missed the mark in his later period, this film is a shining example of everything the writer/director can do right when he's firing on all cylinders. He gets revelatory, surprising, Oscar-nominated performances out of Sean Penn, as narcissistic fictional guitar player Emmet Ray (transparently based on the legendary Django Reinhardt), and Samantha Morton as mute, adorable Hattie, Emmet’s lover. He uses a faux documentary style to augment the grandeur of Ray’s life and artistry, with smart dialogue that is quippy and fun in one of his best scripts he's ever written that balances dramatic moments equally with comedic ones. But moreover, as a lifelong lover and performer of jazz, this is one of Allen's biggest love letters to the music, myths and larger than life personalities that surround it. [A-]

"Small Time Crooks" (2000)
We're so used to seeing Allen as a neurotic intellectual that it's sometimes refreshing to see him playing at the other end of the spectrum, and his performance in "Small Time Crooks" is only first among a cluster of fully-flung idiots. Riffing, at least in part, on Ealing crime comedies like "The Ladykillers" and "The Lavender Hill Mob," Allen plays Ray, a jailbird who plans to rob a bank next to a bakery, only to discover that the cookies that his wife Frenchy (an excellent Tracey Ullman) has been selling as cover for the heist are far more lucrative. It's an oddly structured piece, like two films crammed into one (the middle act, featuring Hugh Grant as a sleazy artist, parodying the class system, is pretty weak), but it's mostly enjoyable, if uneven. And in a now-rare acting appearance by the great Elaine May, it has one of the great supporting performances in the Allen canon. [C]

“The Curse of the Jade Scorpion” (2001)
Every year brings us a new Woody Allen picture, bringing with it grousing on the side-lines about how the creator of Alvy Singer is scuttling closer to the grave by tarnishing his cinematic legacy. It’s a fixed pattern critics have slid lazily into; the notices for "You Will Meet a Tall Dark Stranger" were often written with the same shit-eating rictus grins on their faces as they were a decade ago for "The Curse of the Jade Scorpion." With the benefit of hindsight, the film’s period setting, slight plot (a magician hypnotises Woody into becoming a jewel thief against his will) and Allen’s subsequent inability to find funding for films produced in America, affirm the now-orthodox decline thesis. So is Allen terrible in the lead role of C.W Briggs, “a shallow, skirt-chasing egomaniac” and “myopic insurance clerk”? Yes. Is there a modicum of sexual tension between he and Helen Hunt, the ‘saucy’ efficiency expert whose feminine wiles are supposedly up the yin-yang? No. Was Allen too old at this stage in his career to be hit on by an earthen, breast-exposing Charlize Theron? Take a guess. [C-]