[5] She subsequently appeared in 1992's television movie Up to No Good playing Denise Harmon, and had several guest-appearances in episodes of shows such as Family Matters, Camp Wilder and Crossroads.

[15] 1997 saw Shelton appear in the romantic comedy Trojan War, opposite Jennifer Love Hewitt,[15] and in the fantasy film Warriors of Virtue, as Princess Elysia.

Francine McDougall's teen crime dark comedy Sugar & Spice,[28] alongside Marla Sokoloff, Melissa George and Mena Suvari, was Shelton's first film as a leading actress.

[37][38] Mick LaSalle for San Francisco Chronicle, nevertheless, felt that the lead actors were "vivid, and the characters they play are clearly delineated", while he pointed out Shelton for having a "nice gravity" portraying her role.

[39] Her final film of 2001 was the comedy Bubble Boy, loosely based on the story of David Vetter, in which she played the love interest of a man living in a sterilized dome (Jake Gyllenhaal).

[40][41] A CNN reviewer found the production to be "stupid and devoid of any redeeming features",[42] but Orndorf felt that Shelton made a "strong impression with her empathetic performance and her glowing good looks".

[43] After focusing on studio features, Shelton appeared in a variety of independent films —she portrayed a troubled modern dancer in the dark comedy Just a Kiss (2002), with Kyra Sedgwick and Marisa Tomei,[44] the dream girl of a mafia debt collector in the drama Dallas 362 (2003), and the love interest of producer Phil Kaufman in the dramedy Grand Theft Parsons (2003).

In 2005, Shelton made a brief but notable appearance as The Customer in the opening sequence of the successful film adaptation of Frank Miller's graphic novel Sin City.

[49] Delighted to work on "playing with the ideas of building suspense" with Rodriguez and Tarantino, who she described as "masters of their craft", she based her character in the female leads in Alfred Hitchcock's movies, specifically Tippi Hedren.

[58][59] In 2009, Shelton played an offbeat tourist, opposite Milla Jovovich and Timothy Olyphant, in the psychological thriller A Perfect Getaway,[60] and landed the leading role of Madeleine Gray, a trendy New York art gallery owner, in the independent comedy (Untitled).

[63][64][65] Roger Ebert remarked that Shelton "has the confidence and presence of a born comedienne",[66] and writing for The New York Times, Stephen Holden stated that she "gives a bright screwball performance that recalls the frisky young Diane Keaton".

[68][69] Joe Neumaier for the New York Daily News considered the film to be a "forced, charmless multi-character [production]",[70] but Tyler Foster of DVD Talk felt that Shelton made a "brief impact" in her role.

[77] The film made US$97 million globally and garnered largely mixed reviews from critics;[78][79] Matthew Turner for View London remarked that Shelton turned in an "enjoyably weird performance".

[80] In The Mighty Macs, an independent sports drama, Shelton reunited with Carla Gugino, taking on the role of Sister Sunday, a nun of Immaculata University and the assistant coach of Cathy Rush.

[91] Shelton played the ill-fated sister of a woman tireless researching for the cure for breast cancer, alongside Samantha Morton and Helen Hunt, in Steven Bernstein's independent drama Decoding Annie Parker (2014), which was released for limited markets.

[96][97][98] While Allison Keene of The Hollywood Reporter highlighted the series' "female lead" and focus on "a women’s issue",[99] James Ponniewozik of Time criticized the decision to introduce Shelton's character as "a woman on the prowl for a baby daddy".