Somewhere between Wall Street's Gordon Gekko and Wonder Boys' Grady Tripp on Michael Douglas' scale of scoundrels lies Ben Kalmen, the proud center of attention in Brian Koppelman and David Levien's Solitary Man. Ben wasn't so scared of sixty -- well-respected as a businessman, well-loved by his family -- until his doctor says that he's not so keen on his EKG. Nothing specific, mind you, but that mere mention of mortality is enough to send Ben out the door and off his path. Several months, a business scandal and a divorce later, Ben's trying to convince himself that his latter-day lifestyle of frequent flings with pretty young things is more of a swan dive than a free fall...

He's a poor husband to college sweetheart Nancy (Susan Sarandon), as evidenced by the divorce. He's a bad father to Susan (Jenna Fischer) -- often asking for her help in covering his rent -- and a worse grandfather to her son, Scotty (Jake Siciliano) -- late to every party and game. He's a faithless boyfriend to the well-connected Jordan (Mary-Louise Parker) and a poor chaperon to her daughter, Allyson (Imogen Poots), when she goes off on a visit to his alma mater (the library bears his name; you can also guess how the poor chaperon/faithless boyfriend roles may overlap here). And once he's back on campus, Ben even manages to serve as ill-advised mentor to dweeby Daniel (Jesse Eisenberg, also starring in this weekend's Holy Rollers).

But Ben isn't necessarily a bad person. He's flawed, to be sure, but so keen on bursting the bubble daily on his short-term relationships that he doesn't realize when he's burning bridges with his long-term ones; his behavior stems from his newfound urge to live in the moment and spirals downward from there. And since Solitary Man dwells almost exclusively on the downward-spiral portion of his life, it's mostly left to Douglas to show us the boyish charm on which his character would've built a career (as some would argue the actor himself has) and also the weary regret that he doesn't have everything to gain, but everything to gain back.

As written by Koppelman (Ocean's Thirteen, The Girlfriend Experience), Ben's journey towards redemption is an admittedly familiar one, perhaps overstuffed with characters willing to guide the protagonist towards an inevitable awakening. (Unmentioned above is the appearance of Danny DeVito as an old school pal of Ben's who has just the type of humble life that our anti-hero should envy, naturally; an appearance made all the more fitting by Douglas and DeVito's frequent collaborations in the past.) But as directed by Koppelman and frequent writing partner Levien, there's a certain grace and maturity to how Ben's problems tie together as his world falls apart that spares the film from devolving into so much finger-wagging, and that balance extends to the ensemble as well.

Sarandon conveys equal parts patience and pity towards her ex; Fischer, meanwhile, grows feasibly frustrated with defending this increasingly unreliable man to her son and her husband. Parker exudes an icy control over their relationship, fully aware of what he really wants out of her and how easily she can deprive him of it, and Poots takes after her on-screen mother when it comes to knowing how to best spite her and Ben both. Eisenberg does fall back on his typically timid ways, but in comes Olivia Thirlby as his girlfriend and surrogate conscience just when it seems that the young man is closest to being led astray and becoming every bit the lonely Lothario that Ben has become. And DeVito, he's sage and sympathetic, if only because he hasn't yet had the chance to be screwed over by his old friend.

It really does come down to Douglas, though, portraying Ben as more of an down-and-out rascal than an out-and-out jerk, and his performance finds and holds that crucial harmony between fearful thoughts and the foolhardy deeds they motivate. And when Douglas reprises the role of Gordon Gekko in the Wall Street sequel this fall, he'll probably be eager to remind us that greed is good, but it's here, as Ben Kalmen, that he convinces us (well, eventually) that being good ultimately brings better dividends.