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In 2018, Wolff starred in the supernatural horror film Hereditary. He will make his directorial debut with The Cat and the Moon, which he is also writing and starring in.

For Wolff's work on The Naked Brothers Band series and film, he obtained a Broadcast Music, Inc. Cable Award in 2007, Audience Award for a Family Feature Film at the Hamptons International Film Festival in 2005, and was nominated for a Young Artist Award both in 2008 and 2009. He also received a Certificate of Outstanding Achievement for Best Actor at the Brooklyn International Film Festival for his lead role in the film HairBrained in 2013. On October 11, 2018, Wolff received the Auteur Award at the San Diego International Film Festival.

Wolff focused his career on film roles, portraying Dzhokhar Tsarnaev in Patriots Day (2016) and John "Derf" Backderf in My Friend Dahmer (2017). His other acting roles include My Big Fat Greek Wedding 2 (2016), Jumanji: Welcome to the Jungle (2017), and Hereditary (2018). Wolff made his directorial debut with the drama film The Cat and the Moon (2019).

In 2015, he starred in the indie drama Coming Through the Rye. In 2016, he had a supporting role in the comedy sequel My Big Fat Greek Wedding 2 and played terrorist Dzhokhar Tsarnaev in the drama Patriots Day, about the Boston Marathon bombing.

He first gained recognition for starring alongside his older brother Nat in the Nickelodeon musical comedy series The Naked Brothers Band (2007–09), which was created by the boys' mother Polly Draper. Wolff and his brother released two soundtrack albums for the series, The Naked Brothers Band and I Don't Want to Go to School, which were co-produced by their father Michael Wolff. Subsequent to the conclusion of the Nickelodeon series, Wolff and his older brother formed a duo called Nat & Alex Wolff, and released the albums Black Sheep (2011) and Public Places (2016). The brothers also co-starred in their mother's comedy-drama film Stella's Last Weekend (2018).

In 2007, he portrayed the young boy in the Fall Out Boy music video "The Take Over, The Breaks Over". Wolff made a cameo in the Nickelodeon TV movie Mr. Troop Mom and the USA police-procedural, comedic television drama Monk, both in 2009. He also starred in his playwriting What Would Woody Do? at The Flea Theater—which was directed by his mother—and the HBO medical drama In Treatment, both in 2010. Wolff later appeared in the comedy film The Sitter (2011) and starred alongside Brendan Fraser in the independent film HairBrained (2012).

Wolff began his acting career at the age of 6 in the 2005 musical comedy film The Naked Brothers Band: The Movie, written and directed by his mother. It was commissioned by Nickelodeon as the pilot to the television series The Naked Brothers Band (2007–2009) which was also created, produced, written and directed by his mother. He contributed lyrics, vocals, and instrumentation for both the film and series; their father produced and supervised the music. The show released two soundtrack albums and the song "Crazy Car" ranked #83 on the Billboard Hot 100 charts.

Alexander Draper Wolff (born November 1, 1997) is an American actor, director, writer, and musician.