[24] In 1988, Madhavan gained a scholarship to represent India as a cultural ambassador from Rajaram College, Kolhapur and spent a year in Stettler, Alberta, Canada, as part of an exchange program with Rotary International.

[34] In early 1996, Madhavan worked on a sandalwood talc advertisement directed by Santosh Sivan, who later recommended him to Mani Ratnam to take part in a screen test for a role in Iruvar (1997).

He became the first debutant actor to be cast by Mani Ratnam in the lead role of a film, and revealed that when he found out that he was set to work with the director he was overcome with a "mixture of excitement, awe, fear and ambition".

Appearing as an unhappy groom trying to halt his wedding, the film received positive reviews and emerged as a commercial success, with Madhavan establishing himself as a bankable actor in South India.

Despite featuring among an ensemble cast and being highly anticipated prior to release, the film failed at the box-office, with critics citing that Madhavan looked "rather bored" with the proceedings.

[61][62] Post-filming, Kamal Haasan revealed that he was impressed with Madhavan's enthusiasm and concentration during the making of the film and thus subsequently signed him on to appear in his production venture, Nala Damayanthi (2003), where he played a Brahmin cook lost in Australia.

[66] He received widespread praise for his depiction, with Baradwaj Rangan of The Hindu claiming that Madhavan outplayed Abhishek Bachchan's interpretation of the character in the Hindi version of the bilingual, Yuva.

[9] Madhavan went on to win the Filmfare Award for the Best Tamil Supporting Actor, while another critic from The Hindu cited that he "sparkles as an anti-hero" and that the "character ought to find a very special place in his repertoire".

[67] Similarly, a critic from Indiaglitz.com stated "Madhavan's daring decision to play a negative character, who gets beaten up black and blue at the end, putting his 'hero' image in peril, has paid off, as he walks away with top honours", while a reviewer from Sify.com labelled him as "terrific".

Featuring in an ensemble cast led by Aamir Khan, Madhavan essayed the guest role of Ajay Singh Rathod, a flight lieutenant, whose death triggers a revolutionary movement against corruption.

The film became a blockbuster and also received critical acclaim, with a reviewer citing that Madhavan acts with "extreme, believable sincerity" dubbing him as "truly a poster boy for India", while another claimed he performed "a weak role with élan".

[80] Madhavan wrote the dialogues, produced and featured in the lead role in Nishikanth Kamat's Evano Oruvan (2007), playing a middle class bank employee who becomes so disgusted with the corruption he faces in his day-to-day life that he becomes a vigilante.

In 2010, Madhavan appeared alongside actors Amitabh Bachchan and Ben Kingsley in Teen Patti (2010) as a young professor, with Adarsh again rating his performance as "excellent", but the film failed at the box office.

[91][92] His two guest appearances in the year also received mixed feedback with his performance in the Telugu anthology film Om Shanti (2010) being praised, while a role in the John Abraham-starrer Jhootha Hi Sahi (2010) drew him criticism.

[93][94] Madhavan then collaborated again with Kamal Haasan and K. S. Ravikumar in the romantic comedy, Manmadan Ambu (2010), playing a wealthy businessman who hires a spy to follow his actress girlfriend on a European cruise tour.

[95][96] His only release in 2011 was the romantic comedy-drama Tanu Weds Manu alongside Kangana Ranaut, which saw him play the role of a sensible doctor hoping to get an arranged marriage with a girl, who has a dramatically diverse personality to him.

[97][98] Madhavan next appeared as a police officer in Linguswamy's Tamil film Vettai (2012), an action entertainer featuring an ensemble cast of Arya, Amala Paul and Sameera Reddy.

Madhavan also met and convinced mixed martial artist Ritika Singh to act in the film after contacting her through Raj Kundra, while he was also credited for contributing as an additional screenplay writer.

His portrayal in the Hindi version, Saala Khadoos, received similar praise with critic Subhash K. Jha stating "this is Madhavan's career-defining performance, he sinks so deep into his role both physically and emotionally, that the actor becomes one with the act".

As a result of their conversations, Madhavan altered his original script to include portions from Narayanan's entire career and his services to the Indian space programme, rather than just matters related to the espionage case and his 1994 arrest.

[156] He has also committed to feature in two films produced by Mediaone Global Entertainment, a family drama shot in London by Mithran R. Jawahar and a biopic of Indian engineer Gopalswamy Doraiswamy Naidu by Krishnakumar Ramakumar.

Securing sponsorship deals with HSBC and Santoor, Madhavan premièred the film across North America and the Middle East before its Indian theatrical release, with the promotion method being used for the first time in Tamil cinema.

[176][177] His early work involved advertisements for brands including Bajaj, Ponds, Fair & Lovely and TVS, before signing a major endorsing deal with Pepsi and marketing company, IMG.

[186] In October 2010, he wrote a letter to the CEO of Kentucky Fried Chicken, on behalf of PETA, urging them to stop mistreatment of birds by the fast-food industry outlets and the killing of animals.

[197][198] Madhavan is one of the few actors in India who garners pan-Indian appeal, with his success in establishing himself in the North and the South Indian film industries, seeing him receive multiple offers as a brand ambassador.

[204] He has appeared at functions as a special guest, and has enjoyed particularly close links with technology company, Sify, whom he signed on as his media partner for all his future releases after expressing satisfaction at the website they created for Rendu.

[210] Madhavan has attended conferences as a motivational speaker, talking about issues including situational awareness and confidence, with a speech delivered at Damodaran Academy of Management, Coimbatore going viral online.

He has also collaborated multiple times with directors Mani Ratnam, Rajkumar Hirani and Aanand Rai, citing that the film makers "understand him well" and share a good "comfort level".

Madhavan is a keen golf player, having played for pleasure alongside actor Amitabh Bachchan and director Mani Ratnam, while also appearing in a celebrity charity event in 2007.

His experiences flying Cessna planes when he was with National Cadet Corps, also led to a passion for aero-modelling, with the actor stating it "justified his decision" to pursue a degree in electronics.