1 Vicky in Yeh Dillagi (1994)
In this retelling of 1954’s Audrey Hepburn romance, Sabrina, Saif Ali Khan was the charming younger brother caught in an awkward love triangle with his brother Vijay, played by Akshay Kumar, and Sapna, played by Kajol. Khan, who had just made his debut two years earlier with Yash Chopra’s Parampara (1992), particularly stood out as the happy-go-lucky sibling who matures for the right reasons.
2 Deepak in Main Khiladi Tu Anari (1994)
Saif Ali Khan teamed up with Akshay Kumar yet again. As the over-eager actor Deepak Kumar, he tails Inspector Karan (Akshay Kumar) to use him as fodder for his next film. Khan played the clueless superstar with ease and became the comedic foil to Kumar’s supercop. The two would go on to star in four more films from Tu Chor Main Sipahi (1996) to Tashan (2008).
3 Sameer in Dil Chahta Hai (2001)
For Farhan Akhtar’s debut film, Saif Ali Khan played Sameer, a confused romantic who was constantly ridiculed by his friends Akash (Aamir Khan) and Sid (Akshaye Kumar). Saif Ali showed off his incredible comedic timing in several hilarious scenes where he tries to win the hand of Pooja (Sonali Kulkarni). Eventually, Sameer ends up being the emotional core of the group who brings the trio back together after a long rift.
4 Rohit in Kal Ho Naa Ho (2003)
Director Nikhil Advani’s emotional romantic drama, set in New York, starred Shah Rukh Khan, Preity Zinta and Saif Ali Khan. As Rohit, the good-natured friend to both Preity’s Naina and Shah Rukh’s Aman, Saif Ali displayed his quiet strengths in the film even as the second lead. It seemed only plausible that he should walk away with the girl and the Filmfare award for Best Supporting Actor in the end.
5 Karan in Hum Tum (2004)
The next year was extremely successful as Saif Ali Khan was convincing as the anti-hero in Ek Hasina Thi and an amiable cartoonist in Kunal Kohli’s Hum Tum. His chemistry with co-star Rani Mukerji was real; the love-hate relationship of their characters at different stages of their lives translated well on screen. More importantly, Saif Ali won his only National award for Best Actor for this film.
6 Shekhar in Parineeta (2005)
Saif Ali Khan continued his good form in the mid-aughts with a string of hits. Among them was the adaptation of Sarat Chandra Chattopadhyay’s 1914 classic novel directed by Pradeep Sarkar. Khan fit in well in the period film, despite usually being typecast in most urban films. He stepped into the role made famous initially by Ashok Kumar in the 1953 version directed by Bimal Roy. Khan played Shekhar, the son of a rich landowner, who rejects his proposal with the lower-class Lolita (Vidya Balan in her Hindi film debut), an orphan who lives with her relatives.
7 Cyrus in Being Cyrus (2006)
Saif Ali Khan embarked on his most different role with Homi Adajania’s debut in English, Being Cyrus. The dark comedy focused on a dysfunctional Parsi family which is shaken up by the arrival of newcomer Cyrus. Khan played both parts of the ever-changing character, telling the audience one thing with his narration but going another way on screen. He managed to hold his own even though he was surrounded by stalwarts like Naseeruddin Shah, Dimple Kapadia and Boman Irani.
8 Ishwar ‘Langda’ Tyagi in Omkara (2006)
Omkara, an Indian re-imagining of William Shakespeare's Othello by Vishal Bhardwaj, brought yet another revelation for Saif Ali Khan fans. As the scheming and devious Langda Tyagi, Khan sets forth a chain of events to take down his mentor Omi (Ajay Devgn) and close rival Kesu (Vivek Oberoi). He showed Tyagi’s simmering menace with casual calculation and stood out amongst the ensemble cast.
9 Jai in Love Aaj Kal (2009)
Saif Ali Khan turned producer with Imtiaz Ali’s romantic comedy with shades of drama woven in. It told the stories of different generations. He played the commitment-phobic Jai and the chivalrous Veer Singh (in flashbacks) who romances Deepika Padukone and Giselli Monteiro respectively. In both roles, he was charm personified. His fresh pairing with Padukone led to future collaborations in Aarakshan (2011), Cocktail (2012) and Race 2 (2013).
10 Boris in Go Goa Gone (2013)
In another home production, Saif Ali Khan aimed to bring a new genre to Indian films, the zom-com. He took on the supporting role of Boris, a Russian vampire slayer, who aids three friends as a zombie apocalypse takes over an island in Goa. Khan’s delivery of the line, “I keel dead peepal” still slays (pun intended).