| 2012 | Made his film debut as acapella-obsessed magician Benji Applebaum in the musical comedy 'Pitch Perfect,' alongside Anna Kendrick, Skylar Astin, and Rebel Wilson, a breakout role that earned him a Teen Choice Award nomination for Choice Movie Scene Stealer. |
| 2016 | Originated the title role in 'Dear Evan Hansen' as the musical, directed by Michael Greif with a score by Benj Pasek and Justin Paul, opened at Broadway's Music Box Theatre and became a critical and commercial phenomenon. |
| 2017 | Won the Tony Award for Best Leading Actor in a Musical for 'Dear Evan Hansen' at age 23, one of the youngest solo winners in the category's history, as the production collected six Tony Awards overall including Best Musical. |
| 2019 | Released debut studio album 'Sing to Me Instead' on Atlantic Records, a twelve-track breakup chronicle he wrote or co-wrote in full, led by early singles 'Bad Habit' and 'Ease My Mind' ahead of its March release. |
| 2019 | Starred as Payton Hobart, a political prodigy with presidential ambitions, in Ryan Murphy's Netflix series 'The Politician,' executive producing alongside co-star Gwyneth Paltrow, who played his adoptive mother, Georgina Hobart. |
| 2021 | Reprised his Tony-winning role in the film adaptation of 'Dear Evan Hansen,' directed by Stephen Chbosky for Universal Pictures, starring alongside Kaitlyn Dever, Amandla Stenberg, Julianne Moore, and Amy Adams in a script by original book writer Steven Levenson. |
| 2023 | Played Leo Frank opposite Micaela Diamond's Lucille in the first Broadway revival of 'Parade' at the Bernard B. Jacobs Theatre, earning a Tony nomination as the Jason Robert Brown musical won Best Revival of a Musical. |
| 2024 | Released third studio album 'Honeymind' on Interscope Records, an Americana-tinged love letter to fiancé Noah Galvin executive produced by Dave Cobb, then launched the 21-city Honeymind Tour following a three-week Palace Theatre residency in New York. |
| 2024 | Married longtime partner Noah Galvin at Pioneer Works in Red Hook, Brooklyn, over Labor Day weekend, capping a three-day celebration steeped in Jewish wedding traditions that began with a Shabbat dinner at the Angel Orensanz Foundation. |
| 2026 | Reunited with Rachel Zegler for a sold-out 25th anniversary staging of 'The Last Five Years' at London's Palladium, conducted by composer Jason Robert Brown and later captured on the live album released via Atlantic Records. |