Playboy:
In 1997, McDougal tried out and won her local Venus Swimwear swimsuit competition in Michigan. Her victory caught the eye of Playboy photographer David Mecey. Soon after that she was approached by Playboy for a test shoot at Playboy Studio West which she accepted. Upon completing her test shoot, she was promptly selected to return for a complete photo and video shoot and chosen as Miss December 1997. Her pictorial, which was shot by photographers Richard Fegley and Stephen Wayda, has a winter theme and its outdoor portion was shot in the snowy fields near Park City, Utah. Her video, the "Playmate Profile", was featured on Playboy TV soon after her magazine debut.
In May 1998, she was announced to have been chosen by Hugh Hefner and fans as Playmate of the Year (PMOY) of 1998 at a luncheon at the Playboy Mansion. As her reward, she was awarded $100,000 and a special edition silver Shelby Series 1 convertible with a customized Michigan license plate "PMOY 98". In contrast to her Playmate pictorial, her PMOY pictorial in the July 1998 issue of Playboy has a tropical theme and its outdoor portion was shot at Saint Lucia. According to her interview in her Playmate of the Year "Video Centerfold" which was released soon after her PMOY issue debuted, she believes her physical imperfections are her "funny" smile, her crooked pinkies which she inherited from her grandfather and her "ugly feet" which she wishes others would not look at. Because of the popularity of the VH1 television series "Pop-up Video" at the time, one of the segments in her PMOY video was done as a Pop-up Video parody filled with factoids about her and Playboy. During her appearance on The Magic Hour to promote her PMOY issue, McDougal demonstrated her signature pose, straddle split on TV in front of a live studio audience. Playboy has continued to publish her material in Playboy Cyber Club, Playboy Special Edition publications and Playboy Videos. In an online chat in 2002, McDougal expressed interest in posing nude for Playboy again if offered.
Post-Playboy:
In March 1999, McDougal became the first woman to appear on the cover of Men's Fitness magazine. Since then she began expanding her career into that of a fitness model by appearing in various fitness and body building magazines such as Muscle & Fitness (January 2000), Physical (June 2004) and Iron Man (October 2005, January 2006 and June 2007). She appeared on the cover of the June 2007 Iron Man with film actor Sebastian Siegel, and in a 10-page pictorial in the January 2006 issue of Iron Man as "Hardbody" of the month. In an interview in the September 2006 issue of Playboy, she stated that her transition to fitness modeling was unintentional.
McDougal appeared in a series of sexy TV commercials for XFL football league on NBC and UPN with the theme of "Cheerleaders". These edgy XFL commercials with implied nudity backfired and caused a controversy as they were deemed too risqué by the media, they were quietly withdrawn before the launch of 2001 XFL inaugural (and final) season.
In 2001, she co-starred with Lisa Dergan in The Arena, a Roger Corman-produced, direct-to-video movie directed by Timur Bekmambetov. The entire production was shot in Russia. In her feature film debut, McDougal's character, Jessemina, is a slave girl who is forced into fighting as a female gladiator in an Ancient Roman colony by its corrupt governor. The role offered McDougal her first opportunity to act in a dramatic role and to demonstrate her physical abilities with the movie's sword fighting sequences. The movie, initially titled Gladiatrix was deemed to be a knockoff of Gladiator. Although the movie was not well received, it has turned into a lesser known cult film.
Many regard her as a favorite Playmate in recent years because of her combination of beauty, "Girl next door" appeal and curvaceous figure, according to a November 2001 Playboy poll in the special edition Sexiest Playmates. In that issue, she was voted "Readers' Choice No.2 Sexiest Playmate of the 1990s" (Pamela Anderson was voted No.1).
Playboy released a limited edition doll in 2002 based on the likeness of McDougal and emphasized that it was an accurate model of her statuesque physique. Her collectors' figure was originally slated to be the first in the series to be released, however it was delayed due to redesigns. She was one of twelve contestants in the search for the new host succeeding Brooke Burke for Wild On! in 2002 (known as Wild Off!). The contest took place at The Palms in Las Vegas. Each contestant was given a "wild" challenge to complete and McDougal's challenge was to dress up as Cleopatra and roam the casino at Caesars Palace in the arms of an actor dressed up as Julius Caesar for a day. She completed her challenge and was considered an early favorite by fellow contestants, but did not advance to the final round of 5 contestants. Cindy Taylor was the eventual winner of Wild Off!.
McDougal collaborated with fantasy sculptor Bill Toma in creating a limited edition bronze statuette titled Warrior Princess in 2003. McDougal posed for Toma in the creative process and the pedestal of each statuette bears her signature.
In spring of 2004, McDougal appeared in a photo spread in the Italian edition of Vogue with fellow Playmates, Pamela Anderson, Audra Lynn and Tishara Cousino. It was a tennis themed men's fashion spread shot in Las Vegas by photographer David LaChapelle. The spread contained her first published nudes since her contract with Playboy expired years ago. She travelled to Japan to be one of the eye candies for Scott Hall and Kevin Nash (The Outsiders) when they wrestled at Yokohama, Japan in May 2004. McDougal also participated in the 50th Anniversary celebrations of Playboy throughout the year at Las Vegas, New York and Moscow with other Playmates past and present.
After winning the local try out in Los Angeles, McDougal advanced to World Wrestling Entertainment's (WWE) RAW Diva Search 2004 special held at the Beacon Theater in New York as one of 28 finalists. The special was televised live on Spike TV with a live audience on July 15, 2004. McDougal, clad in a black bikini, survived 2 rounds of elimination during the 2 hour special, only to be eliminated by the judges in the last round at the end, just prior to the selection of the final 10 contestants eligible for online voting.
McDougal appeared in the 2005 Playmates at Play at the Playboy Mansion swimsuit calendar as the calendar girl of July. The calendar was the inaugural Playmates at Play calendar and it was shot on the grounds of Playboy Mansion in 2004. It was Playboy's first attempt at creating a non-nude swimsuit calendar featuring Playmates similar in style with those from Sports Illustrated Swimsuit Issue. While all Playmates appeared in bikinis in the calendar, McDougal and Hiromi Oshima were the only two Playmates actually wearing only painted on bikinis.
She appeared as one of the interviewees in E! True Hollywood Story of Hugh Hefner first broadcasted on April 9, 2006. McDougal briefly described her experience at the Playboy Mansion when she was Miss December 1997. In summer of 2006, McDougal appeared as a fitness model demonstrating all the exercises in a fitness training DVD with Hollywood celebrity fitness trainer Valerie Waters. In November 2006, she was part of a trio of Playmates (along with Tina Marie Jordan and Katie Lohmann) that appeared in the "Celebrity Playmate Gift Guide" pictorial of Splat magazine, a paintball enthusiasts magazine. The pictorial showcased new paintball products for the 2006 holiday season.
McDougal is interested in pursuing hosting duties of TV or sports shows. She has guest hosted TV programs (Wild On! on E!, VIP Access on Showtime) and appeared in other television programs (such as: Lovespring International, The O'Reilly Factor, Playmate edition of Russian Roulette, etc.) and movies (cameos in Joe Dirt, Charlie's Angels, Grind, The Girl Next Door and Raising Helen), music videos (singer David Lee Roth), various pin-up posters, calendars, magazine covers, advertising campaigns, promotional events, clothing, swimwear and lingerie catalogs following her success as Playmate of the Year.