In music, as in life, self-described Yiddishe Blues singer, Pini Brown, straddles two very different worlds: the Chasidic community in Stamford Hill and the late night jazz clubs of next-door hipster neighbourhood, Dalston. Now 26, the up-and-coming musician, who left the closed Charedi society just three years ago, is the subject of an award-winning short film, Pini on the Roof, which will be screened at the UK Jewish Film Festival next week.

The five-minute film provides a snapshot of Pini’s life and larger-than-life character, showing how he navigates the secular world and how his background and experiences have informed his music and character.

The way we were: Pini Brown

Pini says that from an early age, he knew he didn’t fit in . He was a natural showman, who enjoyed singing and had a talent for music. But in the Jerusalem Ger Charedi community where he grew up, only religious music was permitted. He would spend hours alone, outside in nature, singing to himself and playing rudimentary guitar on a borrowed instrument.

“My mum told me it wasn’t cool to play music,” he recalls. “That’s because community is scared of art and artists. They know artists are open-minded and more likely to leave the religion.”

Pini on a roof

He realised that if he wanted to sing and study music in an acceptable way, he had to train to be a cantor, alongside his yeshiva studies. At 17, he started this training. But whenever he wasn’t in class, he was secretly listening to as much non-religious music as he could get his hands on. He smuggled in MP3s, starting with old records by chazanim who had also worked as actors in Hollywood, such as Moishe Oysher, progressing to Yiddish female group, The Barry Sisters, and working his way through to the American jazz and blues of greats like Ella Fitzgerald. At the same time, he would “jump into recycling bins” and fish out abandoned books, stuffing them into the pockets of his bekishe coat. Sometimes, he’d simply tear out handfuls of pages, because they were easier to hide than entire books. Once, he found a dictionary, and read it from cover to cover.

Quirky dress sense: Pini Brown

At 20, he was sent to live in the UK, where a marriage had been arranged for him. He and his wife had two children but, increasingly dissatisfied with Chasidic life, he was already questioning his future in the community, and the marriage only lasted 18 months. After his divorce, he found a flat in Dalston and slowly began integrating into the secular world. From his living room window, he could climb out onto a flat roof and look across to Stamford Hill – a bridge between his two lives. There, he would sing and play Yiddish songs on his guitar. One day, a passerby shouted, “It’s the fiddler on the roof!” That’s how he got the moniker, ‘Pini on the Roof,’ a reference to the famous film.

While he was still Chasidic, he had begun sneaking out to bars in Dalston to hear music. Some of these bars had spontaneous open mic sessions, allowing him to jump up on stage and sing or jam with other musicians. “I got the chance to play with a guy from Zimbabwe, with someone else who played Reggae. Dalston is a bit like Brooklyn, you’ve got everything there, every culture, every language. I would get up on stage and sing in Yiddish while someone else was playing Reggaeton. I just wanted to see how the old Yiddishe songs went together with the modern beats. My music is about collaboration.”

His musical influences are, unsurprisingly, diverse. “I like to listen to music from different cultures, in different languages. I’m a big fan of Tom Jones – I think his voice is incredible. I also love Connie Francis, but she’s not popular anymore, I don’t even think young people know who she is. But she was a huge inspiration to me. However, Moishe Oysher is always going to be my biggest inspiration.”

Around 18 months ago, he started teaching himself guitar again – no longer in secret – because he felt it was an important skill that would improve his musical ability and knowledge: “As a singer, you need to understand the music you’re singing,  the harmonies and so on. I’m lucky that I’m really quick with music. Give me an instrument and in two hours, I’ll be able to play it.”

Tall and striking, with a quirky dress sense that sometimes still incorporates his coat and shtreimel – now as fashion statement, not uniform –  he quickly became a recognisable and popular figure in East London. “I guess I’m one of the characters,” he says. “People recognise my face and want to get me up on stage.”

Pini Brown on the streets of London

In 2022, he was at a Jewish club night, when he was approached by filmmaker Tilly Wax, who had worked on the documentary, Growing up Jewish. “He was walking around looking like a Chasid,” she recalls. “We chatted and remained in touch and then, a year later, when (co-director) Chaia Crompton-Schreiber and I were looking for ideas to pitch to the UK Jewish Film Shorts Docs fund, I said, ‘There’s this fascinating guy,’ and she said she’d love to meet him. He quickly came on board and it all snowballed from there.”

Chaia says it was a challenge to tell Pini’s story in just five minutes. “We wanted to capture Pini’s essence, his character, his ethos, his outlook on life. He has done something quite brave in choosing a new life for himself, but he doesn’t reject where he’s come from. He sits in the balance between his two lives.”

Suits you, sir: Pini Brown

Tilly feels that other portrayals of people leaving the Chasidic communities, such as Unorthodox, have shown the secular community as entirely good, while the Charedi community is entirely backwards: “What was unique about Pini’s story is that he is so extroverted and outgoing and funny, and he loves part of his heritage, the traditions and food and clothing. He’s still singing in Yiddish and he wants to be a Yiddish singer, not a singer of English music. He’s unique.”

Now working as a professional musician, Pini performs two types of gigs: events like weddings, where he’ll sing classic Yiddish songs, and music venues, where he plays modern arrangements. Although he no longer sings in the style of a chazan, he says he still loves to perform a capella, as well as with a band. And as his reputation grows, he’s playing increasingly bigger and higher-profile venues. Recent appearances have included The British Fashion Council’s Fashion City event at the Museum of London, and the Camden Fringe Festival. His vocals feature on Erran Baron Cohen’s music for the score of Zoom Rockman’s forthcoming feature film, Survivor.

Tilly and Chaia want to tour Pini on the Roof internationally and enter it into festivals. “We want this to be a story that isn’t just viewed by Jewish people,” says Tilly. “It’s a universal message. Pini represents someone who has had the courage to change their life, to take charge and agency. I don’t think he realises how unusual he is.”

Pini is proud of the film, which he says captures a short period of his fast-developing life and career. He claims he isn’t an ambitious person, although he has big dreams: “I want to work with good musicians, to get paid to do music and sing at good events.” He may have started his career by singing on the roof, but for Pini, the only way is up.

Pini on the Roof will be premiering at the East Finchley Phoenix cinema at 8pm on Tuesday 12 November (https://ukjewishfilm.org/event/dangoor-short-doc-fund-premieres/), and there will also be screenings in Manchester, Birmingham, Bath, Brighton, Glasgow, Leeds, Liverpool, and Oxford.

For more information see: https://ukjewishfilm.org/