JESSICA CHASTAIN, actor, producer.

With her cherry hair and Creamsicle complexion, Jessica Chastainpossesses a classical beauty suitable for Victorian high collars (Crimson Peak), to-the-manor-born hauteur (Miss Julie), heroic archery (The Huntsman: Winter’s War), and parts requiring her to keep her dimpled chin cocked. Chastain has also dived into the netherworlds of counter-intelligence (Zero Dark Thirty) and high-roller underground gambling (Molly’s Game, as real-life “poker princess” Molly Bloom) without losing translucence. On the horizon is perhaps Chastain’s greatest challenge: playing the sainted country-music singer Tammy Wynette in George and Tammy.

Annie Leibovitz and team observe Jessicas Diehl and Chastain. Photograph by Kathryn MacLeod. Photograph by Kathryn MacLeod.

ROBERT DE NIRO, actor, producer, director.

110 films, including The Irishman (2019); two Academy Awards.

It is impossible to determine which is more intimidating: Robert De Niro’s scowl, which in his gangster roles signals a beatdown about to ensue (see GoodFellas), or his jack-o’-lantern smile, which indicates he’s going to relish the beatdown about to ensue (see his Al Capone in The Untouchables). Violence isn’t the only language his characters speak, but it is the one in which they are most articulate, especially in the collaborations with Martin Scorsese, which began with Mean Streets and continue today with The Irishman (Netflix), co-starring, among others, Al Pacino (as Jimmy Hoffa!), Joe Pesci, Harvey Keitel, and Bobby Cannavale—ya gotta problem with that?

HARRISON FORD, actor, producer.

Amazing how far Harrison Ford’s cocky, goofball grin has traveled since he hot-rodded down the main drag in American Graffiti, a grin that would forge a conspiratorial pact with audiences worldwide. Ford’s space jockey, Han Solo, in the Star Wars saga, and whip-cracking Indiana Jones were—and are—joyous throwbacks to the movie serials of lore, their boyish zeal unextinguished by age, gray, and grizzle. Ford also took on mortal danger with a straight mug as Jack Ryan (Patriot Games, Clear and Present Danger), the replicant terminator in Blade Runner, and Dr. Richard Kimble in The Fugitive.

MICHAEL B. JORDAN, actor.

12 films, including Black Panther (2018).

After appearing in a multitude of television series (most impactfully in The Wire), Michael B. Jordan had his big-screen moment of arrival in Ryan Coogler’s Fruitvale Station, a haunter of a film based on a real-life tragedy that illustrated why Black Lives Matter. Since then, Jordan has muscled up into the heavyweight division, literally in Creedand figuratively as Erik Killmonger, not a name to trifle with, in Coogler’s insanely anticipated rollout of the Marvel superhero Black Panther.

Top: V.F. features editor Jane Sarkin and Annie Leibovitz review wardrobe options with Jessica Diehl; Bottom: Annie with the photo team and Michael Shannon (seated). Photographs by Kathryn MacLeod. Top: V.F. executive West Coast editor Krista Smith interviews Annie about the Hollywood Portfolio for VF.com; Center: detail of Annie’s on-set office, with photo research and blocking plan. Photographs by Matthias Gaggl (Office, Zendaya), Kathryn Macleod (all others). Top: The photo team adjusts lighting. Center: Gal Gadot arrives on set. Bottom: Michael Shannon sitting on set. Photographs by Kathryn MacLeod.

ZENDAYA, actor, singer.

Another Disney sensation who has gone mainstream massive, Zendaya—star of the Disney Channel’s K. C. Undercover—has zapped the sweet spot in pop culture where entertainment, fashion, and social media meet and cross-pollinate. She glammed down to play a dorky misfit in Spider-Man: Homecoming, then twirled up to loop the air as a trapeze artist in The Greatest Showman, as if to say, “Why should Spidey get to do all the swinging?”

MICHAEL SHANNON, actor, musician.

Everything Michael Shannon is in, he intensifies. As the lawman in Nocturnal Animals, Shannon was an avenging angel in a white Stetson hat; in the keenly anticipated mini-series Waco, a docudrama depicting the siege of the Branch Davidian compound, Shannon’s resolute F.B.I. negotiator faces off against a crackpot messiah (Taylor Kitsch’s David Koresh); and in 12 Strong, he and Chris Hemsworth take on the Taliban. Small or big, there’s no theater of conflict he can’t command.

Annie sets up the first panel of the cover, with Oprah Winfrey, Tom Hanks, and Reese Witherspoon. Photograph by Kathryn MacLeod. Photograph by Kathryn MacLeod.

OPRAH WINFREY, actor, producer, philanthropist.

Oprah enrings the earth. Television host, author, producer, magazine publisher, powerhouse actress (The Color Purple, Beloved, Lee Daniels’ The Butler, Selma, The Immortal Life of Henrietta Lacks), influencer without equal, and the first black woman to win the Golden Globes’ Cecil B. DeMille Award, Winfrey is more than the sum of her accomplishments—she’s a gravitational field that doesn’t press down but lifts up. Everything she does is dedicated to betterment without being didactic or, worse, corny. Will Oprah’s next act be a presidential bid?