It was a performance that could have made her little more than 'Maxim'-type magazine cover fodder for the a few months. But in 1999 Richards followed it up with a role as a high school pageant queen in the mockumentary 'Drop Dead Gorgeous,' an uneven but often hilarious film that pitted Richards alongside a strong ensemble of comic talent -- Kirsten Dunst, Brittany Murphy, Amy Adams, Allison Janney, Ellen Barkin, and Kirstie Alley in maybe her last, non-annoying screen appearance as a fame-rabid show mom.
Richards' gun-toting Becky Ann Leman was one of the biggest surprises of the whole film (her beauty show talent: slow-dancing with a crucified Jesus doll), if only because Richards showed a keen ability to play against type, to embody the typical "hot girl" concept while at the same time reminding us of how silly that concept is.
Richards followed that up with supporting roles in fare like 'Tail Lights Fade' and 'Undercover Brother' (where she was once again cast, perfectly, as the temptress White She Devil), and made the occasional foray into TV, such as her hilarious stint on 'Friends' in 2001, as the Gellar cousin who tortures Ross with the love that dare not speak its name.
It wasn't until she played Dr. Christmas Jones in the Bond flick 'The World Is Not Enough' that things seemed to go a little downhill for Richards. While Pierce Brosnan's tongue-in-cheek Bond films featured a roster of well-known actresses as the historically throwaway Bond girls (Teri Hatcher, Michelle Yeoh, Minnie Driver, Famke Janssen, and most famously, Halle Berry), Richards was the only one who failed to come away with some sort of ironic, pop-cultural cultural cred for her performance. As Yeoh went on to 'Crouching Tiger, Hidden Dragon', Hatcher to "Desperate Housewives' and Berry to Oscar gold for 'Monster's Ball,' Richards ended up alongside Luke Wilson in the little seen rom-com 'The Third Wheel'.
But the real point of no return came with Richards' 2002 marriage to that beacon of Hollywood class, Charlie Sheen. For the next three years, we heard from her only when she'd been embroiled in some high profile, domestic scuffle: there were kiddie porn accusations, death threats, restraining orders, and that bizarre, Springer-esque couple swap with Richie Sambora and Heather Locklear. Its no coincidence that her on-screen success ended when that marriage did, in 2006.
Aside from bit parts in the ensemble pieces 'Love Actually' and 'Scary Movie 3,' since then its been one doomed project after another for Denise Richards. Anyone remember 'Blonde & Blonder'? No? How about 'Finding Bliss'?
In 2008 Richards did what many before her had to re-spark their withering careers: she turned to reality television. But once again her off-screen entanglements with Sheen proved an obstacle. 'Denise Richards: It's Complicated' featured the star making trips to the DMV, coping with insomnia, and dealing with the death of her mother, but Sheen's legal move to block his ex from showing their kids on screen and his resulting campaign to boycott the show (coupled with terrible reviews) caused E! to put the show on ice after just two seasons.
Which brings us to saddest irony of Richards' recent turn in 'Deep In the Valley', which isn't the naked commentary or the direct-to-DVD release. Among her co-stars is current E! reality show queen Kim Kardashian, whose show, unlike Richards', is still going strong for whatever reason. The real difference between the two is a matter of progress, the old guard meeting the new. Kardashian's role is a small one, and yes, it's in a less-than-stellar film. But it's the result of a young career built from the same kind of off-screen scandals that ruined Richards', making 'Deep In the Valley' a step-up for one young sex symbol, and a step back for an aging one. Now nearing her forties, is there a way for Denise Richards to turn it around?