Jack Flanagan and the Eternal Sunshine of the Spotless Mind

A decade ago, Flanagan was playing a solo showcase for Richard O'Donovan, Polydor’s Head of A&R, with a backing band that included his friends Charles Watson of Slow Club and Mystery Jet Blaine Harrison. “At the end, it was ‘Cool, give him some money, he's going to go and do some demos.’ The version of a song from that session, “Boys and Girls”, is finally about be released on Rides The Sky, because instead opting for a solo career, one of his backing band had a very different idea for what Flanagan should do next.

“I was driving away with Blaine from that showcase and he said, ‘How do you feel about joining Mystery Jets?’ I remember looking at him and saying, ‘I love your band.’ They were my favourite band when I was at school, so I thought, ‘Do I have a slow burn solo career, or do I join a band that I love?’ I glad I didn't go down the road of my own stuff then, because at that point I didn't really know how to sing or play. I could just do enough to write a song, so to join a band like Mystery Jets was like going to music school.”

When I meet Flanagan in a hotel in Kings Cross, he’s just played another solo showcase earlier that afternoon, but this time in markedly different circumstances, Harrison was in the audience rather than onstage with his friend, and instead of taking his first tentative steps as a songwriter, as he did for his audition for Polydor, he’s about to release an album, Rides The Sky, a brilliant collection of songs and stories.

Today’s showcase followed his debut solo shows the previous week, where he found himself in the unusual position of being both the support act and headliner with Mystery Jets. “They were all at the front watching me every night. The best thing about Mystery Jets is it’s a family and I see my solo music being part of that umbrella”, he explains. “There was a time when I thought about making a solo record - with delusions of grandeur and ego mania - but being part of that band means a lot to me. It took me a while to realise that, and I had to get over myself to realise that. They’re the most supportive friends I could ever have.”

When Flanagan started his musical journey as a teenager, he became aware that his background of growing up on a council estate was at odds with contemporary successful artists, and that the entry point for the music industry had changed. “Lots of people today who are good at music have grown up in an environment with parents who are in the arts or have got lots of money” he tells me, “What money buys you is time and when you've got time, you can learn how to play instruments really well. I didn't have any of that, I just had the need to express myself.”

Meeting Harrison gave Flanagan the chance to be part of a world where creativity was not only possible, but positively encouraged. “Being 21 and meeting Blaine, who was brought up in this beautiful world where he was allowed to create, he took me into that, I learned so much from it and that's where I’ve got to now.”

Strapping on an acoustic guitar to play songs from the Rides The Sky for the first time live has also prompted Flanagan to reappraise who he is as a solo artist. “What I really liked about the tour with Mystery Jets was going out to a half full room and just playing. I grew up listening to folk music, but I never thought of myself as a folk singer”, he tells me. “Even though the crowds weren’t as big and people were still coming in, I was sharing stories with them. After each gig I felt really fulfilled, I played these songs I wrote about real things that happened. People reacted to them, and I never thought that would happen. I was like, ‘Fuck, maybe I am a folk singer!’” Flanagan bursts into the first of a series of laughs that punctuate the hour we spend talking. “I discovered that's probably what the strength in my music is now, sharing things that have happened to me with strangers, and hopefully them understanding or relating to it in some way.”

I tell him that Rides the Sky reminds me of Michael Head’s writing, in the way the former Shack frontman’s storytelling unpicked the small, incidental details of everyday events and their significance and consequences. “It's so great that you said Mick Head, he’s one of my favourite songwriters of all time. Shack’s HMS Fable is one of my favourite records of all time. I really love The Pale Fountains, 'Jean's Not Happening', what a song.”

As with all debut albums, Rides The Sky is the first step in an artist’s story, but the key difference is that it was written before and alongside his current band Mystery Jets. Flanagan didn’t think he’d ever release the songs he was working on outside of the band, however like Blaine Harrison’s plan at Flanagan’s first solo showcase, his manager Roger – a mainstay in his life since he was eighteen – also had a different idea for a path he could take.

Flanagan became a father three years ago, but when his relationship with the mother of his child ended, he initially crashed at friends’ houses - “It was weird being in a semi successful band and going back to sofa surfing again” - before Roger told Flanagan he could stay with him, and he’s lived there ever since. After he’d moved in however, he wondered if his manager was losing interest in the songs he’d been working on. “I was sending him new songs and he wasn’t really commenting on them” he explains, “and then out of nowhere, he compiled the album, track-listed it and put artwork on it. It isn't the artwork that it is now, but he demoed it all up. And then within two weeks, I had a record deal.”

Roger’s intervention came at exactly the right time for Flanagan. When he first started writing songs, he found himself questioning whether they were good enough to be heard by the outside world, but as the years progressed, he started to settle into his own skin as a storyteller. “The thing about all of these songs is they that had to come out of the bag. Too many people were telling me that I should release them and then my manager forcefully did it.”

The finished result is a soundtrack of Flanagan’s life from his late teens to the present day. Rides The Sky is full of personal, but universal stories which take in the ups and downs of relationships, hedonism, breakups, becoming a father and coming to terms with oneself. “A lot of these songs are tied in with infatuations I've had with people or situations. I can only really write about myself and they're all stories about myself - love stories, and stories about messing up.”

A case in point is “Misty”, written about the songwriter Misty Miller, which encapsulates Flanagan’s candour as a storyteller. Instead of changing the titular character’s name, the autobiographical nature of the story brings the listener into the evening he and Miller had their first and only date. “Pretty much everything word for word in the song is true. I went to a gig, watched her play and fell in love with her. We met at the bar and had a drink, we had a kiss at the end of the night, and it was the most beautiful thing ever. But that was it, nothing ever happened again.” When I ask him why they didn’t go on a second date, he laughs and says, “I think I was a bit too keen afterwards in the text messages. I'm really not very good at them! I’m really lucky now, because she's my friend. I saw her play yesterday and it was amazing. I love her music, and part of what I felt for her was a strong connection with her songs.”

Flanagan’s path to becoming a songwriter began in a childhood full of movement. He grew up on a council estate in Basingstoke and went to a Catholic school, “because the other schools were too rough. The Catholic school was shit for its own reasons, but it was better than the ones where you’d get beaten up. I had a pretty normal upbringing. I had a lot of friends and had a nice time being a kid.” When he was 16, he was set to go to the tech college in Basingstoke, but his parents got divorced, which he reflects, “Is probably everybody's story. And then I moved to Salisbury.” His Mum got a job as the principal of the local college, but instead of knuckling down to academic study, Flanagan discovered that youthful rebellion was an irresistible path to take.

“I discovered smoking weed and it was the best thing ever” he tells me, “Your parents are splitting up, there's loads of weird stuff and your life’s changing. I was like, ‘Hold on a minute. There's this thing I can smoke that makes me feel really great?’ I started smoking it all the time. I was doing it for breakfast. I took it really far at 16 years old. I don't smoke anymore, it drives me loopy. But I was really good at it.”

His initiation to weed came via a schoolmate called Oli. “He was this beautiful kid who loved Procol Harum and Jefferson Airplane. He had this little Ford Fiesta and we used to sit in it smoking with a plastic bag and a plastic bottle.” Skipping lessons at the school where his Mum was the principle had an inevitable conclusion, albeit one that would set him the road to what he was meant to do. “She expelled me. One day she came out to the car park, I was there with this fucking big thing, smoking in a Ford Fiesta and she said, ‘You're going have to leave the college.’”

His Mum encouraged him to move to London at the age of 16, telling him to “‘get as close as you can to the city and try and make music’, which was really cool of her, she helped me to get me to the city. She knew that I was a bit of a fuckup and that I just wanted to do music.” Finding himself in London’s indie scene, Flanagan met The Holloway’s Rob Skipper and the pair became inseparable. “He was my best friend and he’s my best friend still. People loved him. I loved him.” As with other parts of Flanagan’s story, serendipity played its role, when Flanagan was dating a musician, Leah Mason, who was signed to Polydor. “Her guitarist Johnny was from Basingstoke, where I was from. He said, ‘I've met this guy called Rob, you should be in a band with him.’ I was 17 and I was like ‘This guy's a rock star, he's toured the world.’ We got really close.”

The pair formed a band called Hares, but their friendship also embraced hedonism with tragic consequences. “I remember we were in a bar in Brick Lane and fell into the drug thing. I didn't get addicted to it, but he got addicted to it and it killed him.” Skipper eventually managed to quit his habit, but a relapse led to a fatal overdose in 2014, at the age of 28. “It turned my whole life upside down because it was my brother and closest friend. He was the second part of my soul and I lost him.”

Eight years on, Flanagan is still coming to terms with his friends passing. Last year on the anniversary of Skipper’s death, he woke up from a bad dream unaware of the significance of the date. “I had this weird dream that someone wasn’t right and then I got texts from people saying, ‘It's the anniversary.’ There's something in my body that remembered it and I've never had anything like that before. It was like this shock memory. It really fucked me up because I miss him a lot, but he’s survived by his lovely daughter and his widow, who is amazing.”

Flanagan started writing the oldest songs on Rides The Sky “when I quit the band because I kicked it and he couldn’t. I started writing 'Blue Canoe' when I realised I couldn't be in a band with him anymore. I thought he'd be alright.” “Blue Canoe” is a song keystone of Rides The Sky, a sparse, blues song that summons the spirit of Fleetwood Mac’s “Albatross.” Flanagan tells me that “Even now, all of my friends say it's the best song on the album, everyone unanimously says it.” As wondrous as “Blue Canoe” is, when I tell Flanagan that it’s not my favourite song on the record, he laughs and says “Thank God! I was worried that my first one was always going be my best one.”

On an album of repeated delights, it’s the closing “Why Am I Only Here” that sees him hit his peak stride as a writer. Flanagan was listening to “a lot of Harry Nilsson” when he wrote it, and I tell him I thought that it sounded like a blend of Nilsson’s “The Moonbeam Song” and “Happy Xmas (War Is Over)” by John and Yoko. “Both of those songs were on the mood board when I did that song, it’s cool that you said that," he tells me.

“Why Am I Only Here”, co-written with his friend Martin, who plays guitar with Spiritualized, tells a story of each of them of being in stasis. Martin was due in the studio for a session with Flanagan, but having started his day with a joint, he arrived late, telling Flanagan he’d gotten to the end of his street and felt like he’d been walking for hours, and his only thought was ‘Why am I only here?’ Hearing the phrase, Flanagan told Martin they had to write a song with that title there and then. “At the time I was splitting up with the mother of my kid, so I wrote the first half, which is this very personal message to her, and then he wrote the end, which is about him smoking too much weed and not realising where he was!”

Other songs take in equally personal stories. “Something Has Changed” was written about being away from his daughter during lockdown. “It was the longest I hadn't seen her for ages, so I felt really sad and I wrote her that song. She’s my best mate.” “Don’t Ask Me Why” documents the life of a woman Flanagan had a brief relationship with. “She was an amazing girl. She lived with a dominatrix, which is the line “Tied up in chains.” It was a strange time, she was a very fleeting part of my life, but I felt so compelled to write about her because she lives on the outside of normality” he reflects, “I didn't want it to end, but I knew it had to because I couldn't keep up with her.”

After a ten year wait to release his first solo album, Flanagan has already written most of record number two. “I love Tom Petty, he's a complete storyteller and I'm trying to adopt that method with the next record, not in the sense of ‘it's an Americana record’, but that whole narrative going on.” Having delved deeply into his psyche and demons on Rides The Sky, Flanagan wants to explore other sides of himself on his next album. “I'm not guarded. As a person I give everything. I'm quite impulsive and I don't hold things back from people when I meet them. So to try and not be like that in my songwriting feels counterintuitive, but on the next record I'm trying to find the lighter parts of my personality.”

I tell him that reminds me of a line from Rides The Sky’s opening song, “Curses” - “Curses become your friends.” Is it about the idea of accepting that things can and will go wrong in life? “It’s accepting the fact that everything's going really wrong in your life and making peace with the aftermath of it. Something cool happens and then a load of shit things happen. You mess a few things up, and then something else cool happens”, he explains. “Luckily, the well of inspiration hasn’t dried up. I think it's part of my shtick that I’m secretly confident. I have these waves of self-belief, especially more so now.”

Has playing solo shows helped with that, where there’s nowhere to hide and it’s all on you? “It's exactly that. And I didn't realise that until a week ago when I did it for the first time. Now I want to keep doing it. I've got put band together who are brilliant but for this initial period, because the songs are so personal, the best way to get the message out is by standing with an acoustic guitar and trying to make people listen to it.”

As we wrap up, with Flanagan on his way to pick up his daughter, he reflects on how far he’s come since he wrote “Blue Canoe”, both as a person and as a writer, and how rather than Rides The Sky marking the end of a chapter, it’s instead the start of his next story. “With a lot of the songs on the album I was in a place where I wasn’t happy in my own skin. All of this weird stuff was happening in my life, and I felt like I was cursed. But now the album’s coming out, I feel so at peace with it. I keep having these moments now which never I used to. Before, I used spend time on my own thinking ‘Everything's rubbish’, but now I'm sat having a beer with you, and thinking ‘This is fucking brilliant.’ I’m a good place now.”