He has made two audio documentaries for the Wellcome Trust: Homesickness in the Modern Age and The worst sound in the world.

He is a member of the poetry collective Aisle16, who run Homework, a monthly night of literary cabaret at Bethnal Green Working Men's Club.

His 2021 collection A Supermarket Love Story, also published by Go Faster Stripe, included The Alcohol Aisle which was longlisted for the 2020 National Poetry Competition.

In an article of The Top One Hundred influential alumni from the University of East Anglia, Osborne is ranked 99.

[9] He presents Stress Test, a monthly poetry show on Soho Radio, alongside Martha Sprackland and Joe Dunthorne.

(2010), John Peel's Shed (2011), Aisle16 r Kool (2011), On The Beach (2013), Most People Aren't That Happy, Anyway (2015), Circled in The Radio Times (2017) and You're in a Bad Way (2019) and 'My Car Plays Tapes' (2021).

In 2010 he presented a show on the Norwich community station Future Radio where he played some of his favourite tracks from the collection.

This was then turned into John Peel's Shed—a stage show for the 2011 Edinburgh Fringe festival, where it enjoyed a complete sell out and five star reviews.

In 2019, You're in a Bad Way, a storytelling show about music, dementia and getting older was performed at the Voodoo Rooms at the Edinburgh Festival Fringe.

In 2021, My Car Plays Tapes, his fifth theatre show, debuted at the Edinburgh festival, performed at a specially made Covid friendly stage at Summerhall.

John has been reviewed by prominent journalists and publications including: Gillian Reynolds of The Daily Telegraph,[2] The Observer,[11] Martin Kelner for The Guardian,[12] and Fordyce Maxwell on Scotland on Sunday.