Since leaving Hamilton, he played a recurring role in the television series Black-ish (2016–2018) and co-starred in the films Wonder (2017), Velvet Buzzsaw (2019) and The Little Mermaid (2023).

Diggs also wrote, produced, and starred in the 2018 film Blindspotting, which earned him a nomination for the Independent Spirit Award for Best Male Lead; he acted as creator, writer, and executive producer on the 2021 spin-off sequel television series Blindspotting, in which he also reprised his role as a guest.

[5] In 2021, he received a nomination for a Primetime Emmy Award for Outstanding Actor in a Supporting Role in a Limited Series or Movie for his performance in the Disney+ live stage recording of Hamilton which was released in 2020.

"[9] His parents' ethnic and racial identities have contributed to his own self-identification: "The cultures never seemed separate—I had a lot of mixed friends.

"[10] Diggs is an alumnus of Berkeley High School and Brown University, where he graduated in 2004 with a bachelor's degree[11] in theatre arts.

[15] Diggs performed in experimental theater early in his career, most notably when he was on the national tour for Marc Bamuthi Joseph's choreopoem, Word Becomes Flesh, about a nine-month pregnancy through the eyes of a young, single father.

In 2017, they released The Deep, a five-and-a-half minute track that tells the story of a society of slave descendants living underwater.

Diggs is a member of True Neutral Crew, with Brian Kinsman, Margot Padilla, and Signor Benedick the Moor.

[29] Two years later, in 2012, he released his first solo rap album, Small Things to a Giant, composed of original music he had written.

In December 2020, Diggs, along with lifelong friends William Hutson and Johnathan Snipes, partnered with Disney Channel to produce a festive song for Hanukkah.

Blindspotting the TV series, follows Ashley Rose, portrayed by Jasmine Cephas Jones both in the film and show, as she navigates life after longtime partner Miles is unexpectedly incarcerated.

The series was picked up by Lionsgate Television, produced by Dreams with friends Inc. and Snoot Entertainment, and was distributed by Starz.

Alongside his lifelong friend Rafael Casal, Diggs co-wrote, co-produced, and co-starred in the 2018 film Blindspotting, which premiered at Sundance in January 2018.

Diggs and Casal wrote the film over nine years to tell a story about their quickly gentrifying hometown as they knew it.

[48][49] On May 28, 2017, an honorary Doctor of Fine Arts degree was conferred upon Diggs during the 249th commencement ceremony at Brown University, his alma mater.