Ultra-cool Tom womanizes and boozes his way through the Manhattan hot-spots you've only read about in history books—he sleeps with a bartender at Pravda and has a rendezvous with a model at Bungalow 8. Imagine! And in case we at any point forget that this film is in fact, set in the past, just take a look around (What, what? Tom Cruise and Nicole Kidman's divorce is the top story?—right, it's 2001!). But aside from the minor nostalgic kick to be had from various "remember-when" moments, this film is about as entertaining to watch as the dial-up AOL running man (ohmigod—remember that?).
Hartnett playing a tech-savvy wunderkind is about as believable as that Diane Keaton movie where Keanu Reeves played a doctor. Adam Scott (HBO's Tell Me You Love Me) plays Tom's sensible, less-hip brother/business partner and Rip Torn pops in for about three lines as Tom's disapproving father. But most surprising is David Bowie as the grumpy old-school banker who deflates cocky Tom, with a curt "I don't like your style." And there's a token love interest, the lovely Sarrah (Naomie Harris) who portrays the stock quality-chick who tires of Tom's arrogant, vintage T-shirt-and-blazer-to-work ways.
Beyond a script chock-full of cheesy super-serious lines—"just because I'm smart doesn't mean I'm stupid"—the plot fails to engage because everyone over the age of eight remembers all-too-well that, yes, lots of dot-com millionaires lost their shirts in 2001, and, no, it was no fun. And, frankly, it's even less fun to watch the film version now. Helpful tip: Bring an IT guy as your date, so he can translate when Tom' computer-speak ramblings, and familiarize yourself with some I-banker slang as well, or risk feeling "so third quarter '99." How embarrassing.