[10][11][non-primary source needed] From 2017 to 2018, Bassett appeared in episodic roles in the television shows: Lethal Weapon, Game Shakers, and Dirty John.

[12][8] His first substantial role was in early 2018 as Aidan Peters in the third and final season of the Disney Channel comedy television series Stuck in the Middle.

Club praised Bassett for his talent, musical ability and "handling of dramatic material",[22] while Kayla Cobb of Decider stated that he had significant romantic chemistry with the female lead Olivia Rodrigo;[23] Megan Peters of ComicBook.com wrote that Bassett "[endears] fans with his plucky determination to do Troy justice".

[35][36] Bassett's other ventures in 2019 included: a guest role—as Linus, a recovering teenage drug addict—in the fifteenth season of the television series Grey's Anatomy,[37] and being featured on "Evergreen", a track from American musician August Kamp's debut studio album, 19: The Musical.

In April 2021, he conducted a one-night virtual concert titled "A Night with Joshua Bassett", in which he performed ten songs, including an unreleased song titled "LA", and a cover of "Drops of Jupiter", backed by a full band from EastWest Studios in Los Angeles.

[70][71][72] In February 2022, Bassett released a single titled "Doppelgänger",[73] co-directing the music video for the song with YouTuber and fellow creative Elle Mills.

[74] He co-starred along with actor and dancer Ciara Riley Wilson and social media personality Chelsey Amaro in the music video.

[75][76][77] In April 2022, Bassett starred in a supporting role as Anthony, the protagonist's older brother, in the Disney+ original musical comedy film Better Nate Than Ever, directed and written by Tim Federle and based on his 2013 novel of the same name.

"[83] while Joshua Axelrod of Pittsburgh Post-Gazette wrote that Bassett "sells Anthony's growth as he finally begins to understand his little brother".

[84] In May 2022, Bassett announced his eponymous debut concert tour featuring stops in the United States, Canada, and Europe.

[89][90] In March 2022, Bassett fronted the spring campaign, "Member's Always: Future Together", for clothing retailer American Eagle, alongside Madelyn Cline, Maitreyi Ramakrishnan, Michael Evans Behling, Coco Gauff, and Mxmtoon.

Current charities that his merchandise store supports include Bring Change to Mind, Teen Line, and Sunrise Movement.

[93] Other charities that Bassett's merchandise store has supported include Court Appointed Special Advocates,[94] Jack.org, The Young Feminist Fund, and A Long Walk Home.

[97][98] Additionally, Bassett donated a portion of every VIP ticket for his upcoming American/European tour to a charity of the buyer's choice.

[102] In August 2022, Bassett was included on the Variety Power of Young Hollywood Impact List and invited to a gala hosted in partnership with Facebook Gaming.

He, along with friends and family, have worked to create care packages with hygiene and menstrual products, food, clothes, and other essential goods to give to the homeless community in Los Angeles.

[106][non-primary source needed] Bassett sings and plays piano, guitar, ukulele, bass, drums, and some saxophone.

[109][110][111] In January 2021, Bassett became seriously ill and was hospitalized with septic shock and heart failure: "[The doctors] told me that I had a 30% chance of survival.

[114] In December 2021, Bassett stated that he was routinely abused in his childhood by a family member and in his adolescence by a different unnamed older man.