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How time caught up to the comedy of Ben Stiller


In the bombardment of contemporary streaming content from horror splatters to independent dramas, there is a consistent ommitence of one genre, in particular, the comedy showcase. You know, the classic noughties comedies that occupy the DVD shelves of every family home and charity shop bargain bin, the likes of Zoolander, Dodgeball and The Watch that helped to define the landscape of comedy at the turn of the 21st century. It’s no coincidence that such films have since been phased out from the existence of Hollywood, with Ben Stiller, Vince Vaughn and others held as relics to an era long since gone. 

The turn of the new millennium was certainly a simpler time, one that had not yet been marred by the cynical influence of social media, though was certainly being swayed by its imminent influence. Comedies were similar to that of modern cinema and television, with inherently silly plots and elaborate set pieces, helmed by a boys club led by actor and director Ben Stiller who pioneered the comedy landscape of the noughties. 

Rising to popularity in the late 1980s, Stiller found fame on Saturday Night Live as a writer and a featured performer before creating the successful short film Elvis Stories and earning his very own slot on Fox Network with The Ben Stiller Show. Though Stiller was far more interested in directing drama, he found his first taste of success in a leading role in There’s Something About Mary, a film that would catapult him to cultural prominence.

Quickly becoming the face of American comedy, a role in Meet the Parents alongside Robert De Niro would follow before his big break in 2001 with Zoolander. Perfectly typifying the state of contemporary comedy, Zoolander boasted an impressive ensemble cast including Owen Wilson and Will Ferrell, perpetuating the need for silly, puerile humour in modern Hollywood. The film became the perfect conduit to transition the comedy of the erratic nineties to the modern-day, showcasing an equally strange plot with a surreal contemporary edge.

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Such led Ben Stiller on a winning run of similar comedies that put emphasis on eccentric, vibrant characters, taking the Derek Zoolander that made Zoolander so popular and repurposing it for the likes of White Goodman in Dodgeball and much of the ensemble case in Starsky and Hutch. Based on the 1980s cop drama, Starsky and Hutch saw Stiller star alongside Owen Wilson once more, in a film that would represent one of the actor’s final moments of glory, before he would hand the baton over to his co-star Will Ferrell. 

Following a successful 2004, it was at the midpoint of the decade when Stiller’s prominence would begin to dwindle, with flops like The Heartbreak Kid marking an early sign of troubles to come for the once-beloved actor. 

Tropic Thunder marked a beacon of hope before the actor plummeted to irrelevancy, with the likes of Tower Heist and The Watch acting as mere echoes of the actor’s once iconic brand of comedy. Whilst these films dug the grave for Ben Stiller’s brand of comedy, it was Zoolander 2 that laid his fate to rest, with the visibly tired film attempting to recapture the revolutionary nature of the original film with an abundance of cameos and eye-rolling moments. 

With the industry screaming for similar comedic talents, the death of Ben Stiller’s brand of comedy shows just how outdated the format became, refusing to modernise with the ever-changing tastes of the zeitgeist. Zoolander 2 notably marked the final comedy showcase of Ben Stiller and for good reason too, as whilst the world was laughing at the likes of Bojack Horseman, Brooklyn 99 and Rick and Morty, Stiller was trying to retread old ground. 

Standing as a living microcosm of early noughties comedy, the likes of Dodgeball and Zoolander still hold their own thanks to some excellent ensemble performances and ingeniously silly central stories. It was Ben Stiller’s refusal to modernise that led his brand of comedy to eventually ebb away from relevance, with Zoolander 2 a dour gravestone to its modern legacy. 

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