Many movie buffs consider 1999 to be one of the greatest single years of cinema ever. Industry-changing blockbusters, like The Matrix, and daring indies, like The Blair Witch Project, closed out the 20th century with a roar, heralding the new millennium. And once the calendar turned, Y2K fears gave way to excitement, as a young class of auteurs made their way up in the business and technological advancements pushed tentpole studio filmmaking into previously unimagined visual frontiers. It was a thrilling time to be a film fan, and the generation now taking the creative reins of Hollywood as executives and filmmakers was directly shaped by that epoch.

Today’s rising stars of stage and screen were mere children at the time. But they’ve come to know “the classics”—sigh—thanks to their elders and their curiosity as artists, not to mention the algorithmic tutelage of streaming-service recommendations. For this portfolio, which was inspired by vintage-era hair and makeup tests, a bevy of up-and-coming talent helps us pay homage to the iconography of recent yesteryear, bringing to new life the diamond-draped lavishness of Moulin Rouge!, the jockish sex appeal of Love & Basketball, the defiant pink of Elle Woods, and the terrifying business basic of Patrick Bateman. Some of these movies are among the young stars’ favorites. Ours too. —Richard Lawson

Legally Blonde

The singer, actor, and meme queen channels the beloved hero from the 2001 rom-com about an unlikely Harvard Law student, a Chihuahua, and a dream.

The Matrix

The Riverdale heartthrob watched the Wachowskis’ 1999 blockbuster on VHS every day after school. Now it’s his turn to enter the Matrix.

The Royal Tenenbaums

The real-life couple—she’s a model, he’s an actor—take on the iconic stylings of Wes Anderson’s 2001 film about the mixed blessing known as family.

The Virgin Suicides

They’re on wildly different shows (The White Lotus, Riverdale, Cruel Summer, and Mare of Easttown), but there’s a film they all love: Sofia Coppola’s 1999 haunting directorial-debut feature about the deep waters of adolescence.

American Psycho

Already American royalty, the actor, model, and entrepreneur evokes a sinister side in a tribute to Mary Harron’s 2000 satire of the predatory nature of capitalist culture.

Love & Basketball

The model-entrepreneur—and son of Snoop Dogg—has been in the public eye since his days as a wide receiver at UCLA, though in this role he’s chasing hoop dreams.

The star of Euphoria and The Suicide Squad channels the other of two childhood friends with big ambitions on and off the court.

Moulin Rouge!

The triple-threat pop star steps into Nicole Kidman’s glittering role in Baz Luhrmann’s 2001 fantasia.

Mulholland Dr.

Thanks to TikTok—a platform so weird and ingenious that David Lynch might have invented it—Rae is a new kind of ingenue, with a music and movie career on the rise.

Hedwig and the Angry Inch

The singer-songwriter and her mom used to sing songs from John Cameron Mitchell’s 2001 cult classic in the car: “It’s one of the most important movies in my life.”

Throughout: hair products by VIP Luxury Hair Care (Normani); hairpieces by Glam Seamless (Holt, King Princess, Palmer, Palvin, Rae, Spaeny, Sprouse); makeup products by Giorgio Armani (Palvin), Item Beauty (Rae), Maybelline (Reid), Urban Decay (Normani), and Chanel (all other women); nail enamel by Giorgio Armani (Palvin), Maybelline (Reid), and Chanel Le Vernis (all other women except Normani); grooming products by Boy de Chanel.  Hair, Ashanti Lation (Normani), Danilo (all others); makeup, Rokael (Normani); makeup and grooming, Kabuki (all others); manicures, Alex Jachno (all women except Normani); beard artist, Sofia Ruiz (Sprouse); tailors, Tatyana Cassanelli, Tatiana Sali; retouching, Studio RM; set design, Robert Doran. Produced on location by Westy Productions. For details, go to vf.com/credits.

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