[3] Khan made his acting debut in Parampara (1993), and had success in the multi-starrers Yeh Dillagi (1994), Main Khiladi Tu Anari (1994), Kachche Dhaage (1999) and Hum Saath-Saath Hain (1999).

Khan also earned critical acclaim for playing a manipulative businessman in Ek Hasina Thi (2004), an apprentice in the English film Being Cyrus (2006) and the Iago character in Omkara (2006).

Between another string of under-performing ventures, Khan was appreciated for headlining Netflix's first original Indian series Sacred Games (2018–2019) and had his highest-grossing releases in the action films Tanhaji (2020) and Devara: Part 1 (2024).

[24] Bollywood Hungama reported that the success of both films proved a breakthrough for Khan, and his performance in Main Khiladi Tu Anari fetched him his first nomination for the Best Supporting Actor at the Filmfare Awards.

His career observed a steady decline through the 1990s; all nine films he starred in—Surakshaa (1995), Ek Tha Raja (1996), Bambai Ka Babu (1996), Tu Chor Main Sipahi (1996), Dil Tera Diwana (1996), Hameshaa (1997), Udaan (1997), Keemat: They Are Back (1998) and Humse Badhkar Kaun (1998)—were commercially unsuccessful.

"[36] In 2001, Khan appeared in Eeshwar Nivas' box office flop Love Ke Liye Kuch Bhi Karega,[37] (a film loosely inspired by the 1996 black comedy Fargo).

Depicting the contemporary routine life of Indian affluent youth, it is set in modern-day urban Mumbai and focuses on a major transitional period in the lives of three young friends.

[50] Writing for Outlook, Komal Nahta described Khan as a "natural" and "extremely endearing", and Ram Kamal Mukherjee from Stardust opined that he was successful in displaying "a gamut of emotions".

[47] In an attempt to avoid typecasting and broaden his range as an actor, Khan starred as Karan Singh Rathod in the 2004 thriller Ek Hasina Thi, a character he described as "a Charles Sobhraj-meets-James Bond kind of a guy".

[40] The film (which marked the debut of Sriram Raghavan) tells the story of a young woman (played by Urmila Matondkar) who meets Khan's character and is subsequently arrested for having links with the underworld.

[23] For his next release, Khan starred opposite Rani Mukerji in Kunal Kohli's Hum Tum, a romantic comedy about two headstrong individuals meeting at different stages of their lives.

The critic Taran Adarsh praised Khan for delivering his third successive performance[67] and Khalid Mohamed noted that he "rescues several untidily written scenes with his neat wit and that flustered [...] facial expression.

[75] Khan next reunited with producer Vidhu Vinod Chopra in the 2007 epic drama Eklavya: The Royal Guard alongside Amitabh Bachchan, Boman Irani, Sharmila Tagore, and Vidya Balan.

[78] Following an appearance in the poorly-received action-comedy Nehlle Pe Dehlla (a production that had been delayed since 2001),[79][80] Khan featured opposite Rani Mukerji in the 2007 family drama Ta Ra Rum Pum.

[81] Writing for Hindustan Times, Khalid Mohamed praised Khan for displaying a new maturity,[82] but Rajeev Masand thought that neither he nor Mukerji "are able to make much of an impression because their characters are so unidimensional and boring.

"[83] Khan achieved further success in 2008, starring in the Abbas–Mustan thriller Race with an ensemble cast including Anil Kapoor, Akshaye Khanna, Bipasha Basu, Katrina Kaif and Sameera Reddy.

[105][106] The critic Rajeev Masand described the film as "a winning cocktail of laugh-out-loud dialogue and well-timed performances by the three leads", and in particular noted Khan's scene with Khemu's character.

[109] Co-starring with an ensemble cast (Ritesh Deshmukh, Ram Kapoor, Bipasha Basu, Tamannaah and Esha Gupta), Khan portrayed three different characters in an attempt to "expand my market" and step out of his comfort zone.

NDTV's Saibal Chatterjee found Khan's character (a struggling writer) to be "a breezy rejig of his Hum Tum and Salaam Namaste persona of a decade ago", and noted that "the many collegiate hook-ups and break-ups he pulls off in Happy Ending do not look completely at odds with the film's purpose.

[113] A review in The Hollywood Reporter noted that Khan was "well cast" and "believable" in his role,[114] and Rachit Gupta of Filmfare described his performance as "a heady mix of bravado and restrained intensity [which] works in parts only.

Cast alongside Shahid Kapoor and Kangana Ranaut, Khan drew inspiration from the mannerisms of his grandfather and the character Darth Vader to portray filmmaker Rustom "Rusi" Billimoria.

[119] Rajeev Masand termed the film "overlong, indulgent to the point of exhaustion", but praised Khan for "imbu[ing] Russi with the swagger and the arrogance of an aristocrat from the forties".

[124][125] Cast alongside Nawazuddin Siddiqui and Radhika Apte, Khan was drawn by the opportunity to be part of a "creative zone, devoid of certain pressures and constraints that one would associate with the kind of films we normally do.

"[126] The show received high critical acclaim;[127][128] Ankur Pathak of HuffPost called it "a sure-shot winner" and took note of Khan's "stellar performance, one that [he] chews on slowly as he disappears into the broken persona of a tormented cop.

Khan worked with Chawla to provide off-screen inputs, and was attracted to the idea of playing the antagonist, describing it as "a devious character" from the Indian epic poetry Mahabharata.

[130] The critic Udita Jhunjhunwala of Mint commended Khan for "blending the right amount of wickedness with willfulness", but Namrata Joshi found him to be "stiff [and] stern ... to communicate a rather facetious sense of menace.

Filming in the barren landscape of rural Rajasthan proved physically daunting for Khan, and in preparation for the role he learned sword-fighting and horse-riding, and worked with a dialect coach to speak in a Rajasthani accent.

He was attracted to the idea of starring in a "larger-than-life" film and felt challenged by Raut's insistence on overplaying his character; he explained that the process left him "very enriched" and he was pleased with the collaboration.

[146] The show opened amid protests and police complaints against its makers for allegedly insulting Hindu deities and hurting the religious sentiments of Hindus,[147][148] following which Zafar cut several scenes and issued an apology.

[187] Analysing his career, the journalist Shomini Sen noted that "[t]he actor was part of some major films in the early 1990s [...] yet critics wrote him of[f] due to lack of a screen presence and poor dialogue delivery.