[citation needed] In 2016, Henderson formed the comedy trio Two Plus Ones with fellow Footlights alumni Luke Sumner and Josh Chana.

Their comedic endeavours included performances at the Edinburgh Fringe, contributions to Comic Relief, and sketches for the children's show So Beano!

In 2019, he gained recognition alongside comedian Adrian Gray for a comedic Twitter thread tracing music charts back to 14,000 BC and playfully answering the question, "What happened to the first four versions of Mambo No.

Unable to perform live due to COVID-19 lockdowns in 2020, Henderson adapted by creating comedy songs and sketches on both his personal and Jazz Emu YouTube channels and social media accounts.

[4] This led to his breakthrough as Jazz Emu, with his song "How to Socialise" being featured on BBC Radio 1 by presenter Greg James, who described him as "a very funny man".

[5] The character of Jazz Emu has a unique persona and backstory, often characterised as a "global sensation", "1970s lothario", or "unlicensed sex therapist".

He adopts a low and smooth voice, an exaggerated pronunciation of words, and a 1970s fashion sense which includes bell-bottoms and platform shoes as well as spectacles with oversized frames.