In 2019, Samuel Bailey’s play Shook marked him out as a distinctive new talent, writing about masculinity, class and friendship. But when he first began life as a playwright, his dramas were, he says, “rip-offs” of works he admired. “The first few plays I wrote were a Sam Shepard western, a Nick Payne Constellations play, and an Annie Baker. I was thinking: ‘Oh, this is what a play is!’” Having grown up on a housing estate in Worcester, Bailey felt reluctant to bring that world on to the stage. “It took me quite a long time to feel like I could write about where I came from and that people would be interested in it, partly because it wasn’t necessarily what I was seeing on stage.” That changed 10 years ago when he met Jesse Jones, who is now directing Bailey’s new play, Sorry, You’re Not a Winner, produced by Paines Plough. Jones read one of his early plays and said Bailey was mimicking other writers. “He asked me ‘What do you want to write about?’ I told him a bit about my background, and he said ‘Why are you not writing about this?’ It took him telling me that the thing that I was ashamed of was actually what was interesting … and it took a while for me to come round [to the idea that] here was something I could tell authentically.” Shook featured three fathers attending a parenting class at a young offender institution. An insightful study of the way men speak to each other and the intimacies they form, it had bags of humour and tenderness. Shook won him the Papatango new writing prize and had a sold-out run at Southwark Playhouse in London, with a West End transfer set for the spring of 2020 (the pandemic stymied that plan). “Shook was personal in the sense that it was about people I grew up with, cared about, and listening to their stories.” His new play, a coming-of-age drama about friendship, leaving home and entering a middle-class milieu, is closer to Bailey’s own lived experience. “I had been wrestling with it for most of my 20s – feeling this conflict between having left home, and not feeling quite comfortable in this place that I exist now – a more middle-class space at university and then a middle-class space in theatre. I felt like I should be really happy because this is what I want to do but something was making me feel on edge at times.” His girlfriend suggested he make sense of this internal conflict by turning it into a play. It begins the night before Liam departs for Oxford University, leaving his best friend Fletch behind. Bailey went to Cardiff University to study philosophy and politics. “It’s not about me but the emotional journey is one that I’ve been on in the sense of coming to terms with where I’m from, where I exist and operate now, and how you marry those two. When you come from a place that is one thing, and are now in a place that is culturally different, how do you align those things in your head?” Bailey was born in Lewisham, south-east London. His parents split up when he was three and his mother raised him alone in Worcester, first working in a pub and then in the charity sector, while his father and stepmother ran a film company in Bristol. Most of his childhood was spent on the estate but he saw glimpses of another world on his trips to Bristol, and observing their work gave him a head start, he feels. He wasn’t sure if he would ever finish Sorry, You’re Not a Winner, after writing the opening scene, or that he wanted to continue working as a playwright at all. “I resisted going along this path until my mid 20s because I’d seen how difficult it was to make creative work.” He had not only seen his parents “struggling massively” to make ends meet but also strained to make enough money himself. Winning the Papatango prize changed that, and now, at the age of 32, he is juggling several commissions, including a film about a lower-league football team with The Full Monty director, Peter Cattaneo, and a TV series about a woman who infiltrates white nationalist terrorist cells based on Julia Ebner’s book Going Dark. With all the shifts in his life, is he still connected to his early life in Worcester? Very much so, he says. His mother still lives there and his childhood friends are important to him. “I’m godfather to two of their children. I was best man at one of their weddings … I’ve always valued those relationships very highly in terms of what they mean to me. But in terms of the way they live their lives and the way I live my life – they’ve got kids, they’ve been settled down for a long time, the structure of their lives is very different to mine.” What is essential for Bailey, in writing about the people with whom he grew up, is to represent them with integrity. “My first responsibility is to make sure this is a play they can come and see and enjoy. I never want to write a play about people back home and think that if they came to see it, they’d feel excluded. So I need to make sure the form and humour relates to who I’m writing about. Otherwise, you get into a position where it’s like, I’ve moved away from home and I’m going to take their stories and put them on stage for primarily middle-class audiences.” Sorry, You’re Not a Winner is at Theatre Royal Plymouth, 24 February to 12 March; Bristol Old Vic, 29 March to 2 April; and Northern Stage, Newcastle, 5 to 9 April.