The curious case of Hindi cinema’s gentleman rogue

The scion of Nawab of Pataudi has always been the wild card — an oddball, if you will — who has carved out his own orbit: wry, sassy, unconventional, and entirely his own. He’s that eccentric in a family portrait, who chooses a martini over chaia noir-inspired indie flick over a blockbuster, and self-deprecating humour over the trappings of machismo.

When Saif described himself as ‘a very private person’ (you will not find him on X or Instagram) in an interview with Rajeev Masand, it was the kind of understatement you’d expect from someone who’d rather discuss philosophy than flex his biceps for the cameras. In another interview, journalist Roshmila Bhattacharya notes that Khan’s range of interests goes beyond the typical gym routines and commercial benchmarks that dominate Bollywood discourse — he is as comfortable talking politics as he is diving into books, sports, or music, without skipping a beat.

This breadth of knowledge and curiosity sets Saif apart, lending his public persona an air of understated sophistication; he’s not your typical Hindi film heartthrob chasing the next six-pack shot but someone who takes up all sorts of roles, even those in which a little arrogance is part of the package, and turns them into masterclasses on how to be both insufferable and irresistible at once.

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The real magic of Saif’s acting chops lies in his refusal to play it safe (pun absolutely intended). He’s the Khan who doesn’t seem to care much about box office juggernauts but still finds a way to dominate conversations with roles that stick. From the bumbling Sameer in Dil Chahta Haiwho turned cluelessness into an art, to the snarling, scheming Langda Tyagi in OmkaraSaif has proven time and again that he’s not afraid to look foolish — or downright villainous — if the part demands it. He’s flirted with zaniness (Go Goa Gone), veered into existential despair (Sacred Games), and even hammed it up gloriously (Tanhaji). This willingness to go for the untried and untested has earned him a credibility that’s hard to come by in a risk-averse industry.

Venturing into darker, riskier roles

Born into a family where cricket and cinema were second nature, Saif could’ve easily coasted on privilege. Son of Mansoor Ali Khan Pataudi and Sharmila Tagore, Saif was born with a silver spoon so shiny it could blind you. Yet somehow, he’s spent the last three decades walking a path so distinct that it feels like Bollywood wouldn’t quite be the same without him. When he started out as the perennial chocolate boy in the 1990s, he looked like he’d be stuck as a sidekick forever.

But instead of falling into obscurity or clinging to outdated formulas, he zigzagged, diving into uncharted waters with an almost mischievous glee. He had a rocky start when he was cast in Rahul Rawail’s Bekhudi (1992), but was replaced due to ‘unprofessionalism’. While working on the film, he met and married actress Amrita Singh, which marked the beginning of his whirlwind personal life.

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His debut, Yash Chopra’s Consultant (1993), failed to gain traction. Critics and audiences seemed baffled by this posh, floppy-haired boy who appeared to be moonlighting as an actor. Was he charming? Sort of. Talented? Undecided. Relatable? Not quite. The industry wasn’t quite sure where to place him. However, he bagged the Filmfare Award for Best Male Debut for Aashiq Awara the same year.

Despite moderate successes like examination (1994), his career largely faltered through the 1990s, with a string of box-office duds that left critics doubting his future in the industry. Besides Consultant, in films like Main Khiladi Tu Anari (1994) what he had to offer was just his juvenile charm. Fast forward a few years, though, and suddenly, he figured out his sweet spot: flawed men who were too charming for their own good.

The early 2000s saw Saif shake off the baggage of his first decade in the industry, thanks largely to his breakout role in Dil Chahta Hai (2001), Farhan Akhtar’s coming-of-age film, in which he plays the hopeless romantic Sameer, a bumbling, refreshingly goofy friend, who’s vulnerable and endearingly inept at love. As Sameer, Saif wasn’t just funny with perfect comic timing — he was the guy everyone wished they could grab a beer with.

This was a Bollywood hero who wasn’t rescuing damsels in distress or flexing his muscles for slow-motion montages. No, Saif was fumbling over words, messing up relationships, and delivering one-liners with a smirk that screamed, “I’m making this up as I go.” No wonder then that it earned him several awards, including a Filmfare trophy for Best Comic Role. It cemented his status as a bankable actor, capable of nuanced performances that resonated with modern audiences.

While subsequent projects like what to say (2000) and anthology thriller Darna hai hai (2003) and Hum Tum (2004, in which he is the quintessential man-child who eventually grows up) saw varied success, Khan’s evolution as a performer was pretty evident. Saif then decided to switch gears and prove he could act — and not just in the ‘say lines convincingly’ kind of way. From there, Saif’s choices became increasingly daring.

In Kal Ho Naa Ho (2003), he played the affable Rohit Patel in a way that made his unrequited love for Preity Zinta’s Naina both relatable and moving. The knack for playing layered characters became Saif’s signature, but it wasn’t until he ventured into darker, riskier roles that his acting prowess truly shone. In Omkara (2006), Vishal Bhardwaj’s adaptation of OthelloSaif shattered every preconception about his range. And Hindi cinema got Langda Tyagi, a grotesque, cunning, kohl-eyed, venom-spewing villain, fuelled by envy and ambition, with an accent so authentic it felt like he’d been marinating in Uttar Pradesh for years. If Bollywood villains were a fine wine, Langda Tyagi would be the vintage everyone wanted in their cellar.

A star on his own terms

A year prior to Omkara, his turn as the foster child-turned-drifter who wheedles his way into a dysfunctional Parsi family in Homi Adajania’s Being Cyrus (2005), his first English-language film, followed the success of Salaam NamasteSiddharth Anand’s quirky take on live-in relationships and pregnancy before marriage et al, and Parineeta, Pradeep Sarkar’s period musical romance, adapted from Sarat Chandra Chattopadhyay’s 1914 Bengali novella. Was Cyrus a hero, a villain, or just a guy caught in the messiness of human existence? Saif didn’t care — he let you figure it out.

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Even when his films do not do well, Saif’s performances often stand out. In another Adajania’s film, Cocktail (2012), he channels his inner Casanova with a twist. Gautam Kapoor might’ve been unendurable in the hands of another actor, but Saif makes the character of a commitment-phobic charmer, flitting between two women, oddly endearing. It’s this ability to humanize even his most flawed characters that makes his filmography so compelling.

His willingness to poke fun at himself is one of things that sets Saif apart. Who else in Bollywood would bleach their hair, don a Russian accent, and take on zombies in Go Goa Gone (2013), Bollywood’s first zombie comedy, directed by Raj Nidimoru and Krishna D.K., collectively known as Raj & DK. Saif’s self-awareness has always been his secret weapon that allows him to walk around with a shrug.

In grand, theatrical roles like Mughal general Udaybhan Rathod of Tanhaji: The Unsung Warrior (2020), Saif imbues the unhinged antagonist with so much flamboyant gusto and elan that the comparison with Jon Snow in Game of Thrones becomes inevitable. As Sartaj Singh in Netflix series Sacred GamesSaif plays a man drowned in self-doubt, plagued by existential crises, and perpetually on the brink of giving up. You can’t help but root for him even when he is being a bit of a mess. As Bhaira in Jr NTR’s Devara Part 1 (2024), his Telugu debut, he brings the unmistakable menace to his role.

Off-screen, Saif is equally fascinating. He’s the guy who can casually quote Hemingway one minute and roast his own film choices the next. His personal life — marriages, divorces, kids, and all — could’ve easily overshadowed his career. However, he’s managed to keep the focus firmly on his work, even if that work sometimes includes baffling missteps like Love Today Tomorrow 2.

At the end of the day, Saif Ali Khan is serious about his craft but never too serious about himself. In an industry obsessed with numbers, he is a bit of an anomaly. He’s not the biggest star, but he’s charted his own path, with constant risk-taking, polishing of his craft, and an unerring instinct for the unusual, unexpected. Saif may be the fourth Khan, but in many ways, he’s in a league of his own.