He created the sell out Edinburgh show John Peel's Shed and has written and performed six half hours storytelling shows for Radio 4.
He is the author of three non-fiction books. His first, Radio Head: Up and Down the Dial of British Radio, was published by Simon & Schuster in May 2009 and was selected as Book of the Week on BBC Radio 4. It was serialised in the Daily Mail and reviewed in The Daily Telegraph, and Scotland on Sunday. His second book, The Newsagent's Window: Adventures in a World of Second-Hand Cars and Lost Cats, was published in April 2010 and was awarded best memoir at the East Anglian Book of the Year awards.
Together with Molly Naylor he created the Sky 1 sitcom After Hours. The theme song was specially recorded by Pete Doherty and is a cover of the Velvet Underground song "After Hours".
The show is about two twenty somethings who have their own radio show on a canal boat in Lincolnshire. It stars Jaime Winstone, Ardal O'Hanlon, Georgina Campbell and John Thomson. After Hours is produced and directed by Craig Cash. The show's first series was first broadcast in autumn 2015.
He is the writer of six Radio 4 half-hour comedy shows including John Peel's Shed (2011), The Newsagent's Window, Valentine's Day (both 2013) and The New Blur Album (2014). John Peel's Shed was an adaptation of Osborne's sell-out Edinburgh show. The Newsagent's Window was "Pick of the Week" in the Radio Times as chosen by journalist Eddie Mair.
Valentine's Day stars Suki Webster, Ann Beach and Isy Suttie, and is the story of a chef, Sean, who recounts his life by looking through his old Valentine's Day cards. The New Blur Album was Radio 4's "Comedy of the Week" and was a life story as told through the release of each new Blur album. In 2015 the shows The Kindness of Strangers and Don't Need the Sunshine were broadcast.
In 2016 he contributed to the Radio 4 shows Short Cuts and Four Thought.
Osborne regularly appears at venues across the country performing poetry. Since 2006 he has performed at the Glastonbury and Latitude festivals, as well as venues such as The Roundhouse, Norwich Arts Centre and Underbelly. 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. Homework has featured performances by Kate Nash, Tim Key and Jon Ronson. Aisle16 have been described by The Sunday Times as "highlights of the spoken word scene".
His first collection of poetry Most People Aren't That Happy, Anyway was published by Nasty Little Press in 2013 and a poem from the collection was highly commended in that year's prestigious Forward Prize. His second collection No-one Cares About Your New Thing was published in 2017 by Go Faster Stripe. He has had poetry published in The Guardian, The Spectator, Rialto and The Big Issue and broadcast on BBC Radio 3, 6Music and Radio 1.
He has been involved in shows at the Edinburgh fringe festival including The Mid 90s la la la (2008), The 100 Greatest Beekeepers in Switzerland, ever! (2010), John Peel's Shed (2011), Aisle16 r Kool (2011), On The Beach (2013), Most People Aren't That Happy, Anyway (2015) and Circled in The Radio Times (2017).
In 2002 Osborne won a box of records in a competition on John Peel's Radio One show. 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 2012 the show completed a sixty date UK tour, including a run at the Soho Theatre and performances at festivals including Latitude, Glastonbury and Green Man.
He later developed new theatre work, including On The Beach, which debuted at the Pleasance Dome at the 2013 Edinburgh festival and Circled in The Radio Times for the 2017 fringe.
John has been reviewed by prominent journalists and publications including: Gillian Reynolds of The Daily Telegraph, The Observer, Martin Kelner for The Guardian',' and Fordyce Maxwell on Scotland on Sunday.
He has appeared as a guest on radio shows including Geoff Lloyd's Absolute Radio Hometime Show, Jeremy Vine on Radio 2, Richard Bacon on 5 Live, Colin Murray on Radio 1, Shaun Keaveny and Stuart Maconie on 6Music, Fred MacAuley on BBC Scotland, The Verb on Radio 3 and Nikki Bedi on the BBC Asian Network. He has also been a guest on an episode of Scroobius Pip's Distraction Pieces podcast.
Osborne has worked in schools and universities in England, Germany and Austria.
Since 2013 he has been a patron of the Dignity in Dying campaign.