American actor and rapper Mahershala Ali has become a household name in the entertainment world within the past decade, but his resume extends far beyond that. Originally a basketball player studying communications in college, Ali pivoted his career after receiving his MFA from NYU in acting. He made his acting debut in NBC’s 2001 crime drama Crossing Jordan, where he was a main character in the first season. Outside a string of television appearances, including The 4400 and House of Cards, Ali shifted more into movie territory.

His first big appearance was in 2008’s The Curious Case of Benjamin Button, and while he gained more attention for his roles in The Hunger Games franchise, his biggest break came with Moonlight. Per NPR, Ali took home the Academy Award for Best Supporting Actor in Moonlight for his well-deserved performance. He then followed this up with Green Book, which he also won the Oscar for, thus making him the first Black actor to take home the same award twice — as well as the first Muslim actor to win an Oscar. These are his best movies, ranked.

8 The Curious Case of Benjamin Button

the curious case of benjamin button
Paramount Pictures

The Curious Case of Benjamin Button is an adaptation of the American author F. Scott Fitzgerald’s short story of the same name. Familiar faces like Brad Pitt, Cate Blanchett, Tilda Swinton, a young Elle Fanning, Mahershala Ali, and Taraji P. Henson are included in this cast roster. A man (Pitt) ages backward, having been born with the appearance of an old man, and when he meets a young girl whose grandmother lives in the same nursing home he’s in, the two will be destined to fall in love. A grand melodrama that spans decades, it drags on at times, but proves rewarding for some viewers.

Related: Most Iconic Roles Brad Pitt Has Ever Played, Ranked

7 Swan Song

Mahershala Ali in Swan Song on Apple TV+
Apple TV+

Not only did Ali star in Swan Song, but he also was one of the movie’s producers. He is Cameron Turner, the average person living the ideal family life at home. But one day, he is diagnosed with a terminal illness, forcing him to make some big decisions. This includes a science fiction element, twisting the story in another direction: he can choose to replace himself with a clone, thus sparing his beloved family the grief of knowing that he is gone for real. Naomie Harris, Awkwafina, and Glenn Close also star in this tender tale.

6 Free State of Jones

Group of men run with muskets.
STX Entertainment

The story behind Free State of Jones is a true one: during the American Civil War, a farmer in Mississippi revolted against the Confederate rule and decided with other army deserters that they would create their own free state. With their scrappy resources and knowledge of the land, it’s up to these rebels to hold out against the Confederate Army trying to shut their radical ideas down. It is a fascinating tale often unknown from the Civil War era, although it can come across as a white savior story to the contemporary eye.

5 Green Book

Two men lean against blue car; one is white, the other Black.

Participant Media

Green Book is the movie that, per Vanity Fair, netted Ali his second Oscar for Best Supporting Actor. It was based on the real-life occurrence of the "Green Book," which advised African-American travelers about places that were friendly towards them and where to avoid. This movie tells the story of an Italian-American driver (Viggo Mortenson) and an African-American pianist (Ali) traveling to the deep South to perform. The two strike up an unlikely friendship despite the backdrop of the Jim Crow era and blatant racism.

4 Hidden Figures

Three Black women stand together.
Fox 2000 PIctures

Hidden Figures, too, tells a true story. Taraji P. Henson, Octavia Spencer, and Janelle Monae star as three Black women working at NASA in the 1960s. Set during the backdrop of the Space Race, the three clearly were outliers in their cohort not only because of their race, but also because they were brilliant mathematicians. They were easily able to solve problems others were unable to, but since they were Black and women, they were seen as inferior. The movie seeks to tell their story, shedding light on some iconic heroes in American history.

Related: Here's 5 Great Films That Fight For Civil Rights

3 The Place Beyond the Pines

Blonde man stands with cigarettes in his mouth.

Sidney Kimmel Entertainment

The crime drama The Place Beyond the Pines unfolds like an epic. Jam-packed with thoughts about fatherhood, legacy, and reminiscing about what the world has lost, it offers many things to think about after. Ryan Gosling stars as a man who discovers he has accidentally fathered a son, but as he begins to descend into a world full of crime and wrongdoing, it all will catch up to him one day. A three-part story, it is a contemporary update to crime films of the 1950s.

2 Spider-Man: Into the Spider-Verse

Spider-Man wearing inverted suit stands on building.
Sony Pictures Releasing

Spider-Man: Into the Spider-Verse was a success when it first was released in 2018. Created by computer animation, the story takes on the now-classic tale of Spider-Man and applies it to an Afro-Latino teenager from New York City. After being bitten by a radioactive spider while in an abandoned subway station, he develops similar powers to Spider-Man. When the real Spider-Man in his timeline dies, it is up to him when a new villain emerges and the fabric of time and space opens up.

1 Moonlight

Little in Moonlight
A24

A24’s Moonlight took home multiple Academy Awards that year at the Oscars, a testament to the strength of its story. It is like a triptych, telling one boy’s coming-of-age in a three-part saga that is both devastating and beautiful. A little boy named Chiron finds a mentor in a drug dealer (Ali) as a child, leading to the dealer telling him that it is okay to be gay, even as his abusive mother chastises him for it. This sets the scene for Chiron’s relationships in the second two parts of the movie, weaving together a heartbreaking story.