Karo, Hum Tum Pe Marte Hain, Mast and Dillagi − were commercial failures. However, Matondkar's performances were generally well received by critics, (nn a review for Jaanam Samjha Karo, Rediff stating, "Urmila is just about the only heroine who can give Karisma a run for her money when it comes to pelvic thrusts"). Her first hit that year was Varma's psychological horror thriller Kaun, opposite Manoj Bajpayee, where she played a nameless character. Khalid Mohamed of The Times of India (who would later cast her in Tehzeeb) wrote, "She rivets the viewer's interest, carrying off entire reels on her shoulders, through a gamut of quicksilver facial expressions. Vulnerable and baffled, she is utterly believable as the traumatised girl-next-door". Matondkar next played the love interest of Sanjay Dutt's character in the action comedy Khoobsurat. It emerged as a box-office hit. During the 2000s, Matondkar revealed strong, dramatic and psychological features in her roles, and delivered a number of critically acclaimed performances. In 2000, Matondkar re-united with Varma for the action Jungle, alongside Fardeen Khan and Sunil Shetty. She played Anu, who is hostaged by the chief of bandits, when he starts liking her. Taran Adarsh of Bollywood Hungama wrote, "Urmila Matondkar is at ease in a role that gives her ample scope to showcase her talent. Her scenes with Durga can easily be singled out, for they have been shot with brilliance." The film was both critically and commercially successful. She next starred opposite Govinda in David Dhawan's romantic comedy Kunwara. The film underperformed at the box office, with a grossing of . The next year, Matondkar portrayed Ria, an obsessed lover, in Rajat Mukherjee's romantic thriller Pyaar Tune Kya Kiya, a film which received critical acclaim. Her performance was highly acclaimed and several critics noted her for showing great emotional range and depth. Taran Adarsh of Bollywood Hungama, in a positive review wrote, "the 'actual hero' of the film is definitely Urmila Matondkar, who will walk away with all laurels at the end of the day. Her career-best performance, she oozes intensity, love, hate, relentlessness and obsessive behaviour with perfection. And despite the fact that her character gets nuttier as the movie tags along, it is to Urmila's credit that we are able to feel for her pathetic persona." Planetbollywood.com described Matondkar as: "The star of the show is Urmila who is simply mind blowing in this film. The film