After 12 years, five albums and four mixtapes, the curtain closes. Nines’ final project, Quit While You’re Ahead, will be his last. And though many are often sceptical about the idea of a rapper retiring, believing that any such promise will eventually be walked back on, the 34-year-old, real name Courtney Leon Freckleton, is serious about his sixth album being his ultimate.
“I ain’t coming back. I don’t care how much money they offer me,” he says, “If I made decisions based off money, I deffo wouldn’t have had the career I have. No money can make me come back.”
For more than a decade, Nines has been a leading name in the rising tide of British rap. Three of his albums are certified gold, another one silver. All landed in the Top 5, while his August 2020 album Crabs in a Bucket, was his first No 1. He has filtered his stories of hustling and hunger in north-west London through a trademark laid-back flow, and a sense of lyricism filled with punchlines and metaphors. The imagery in his videos and short films have often matched the luxury of his music, bringing his street diaries to the screen. In that process, a cult following that started on YouTube has spread across the country, and beyond.
The past few months have been intense for Nines. Making Quit While You’re Ahead took about six months, then after that he bunkered down to shoot videos and the now trademark short film that have accompanied all of his most recent projects. There is a huge show at south-east London’s O2 to prepare for in November, and if the album does well, maybe festivals in summer 2025. Today, we are in the back alleys of a London studio building, mid-afternoon drifting by, reminiscing on the high moments of the past decade.
“Getting paid to travel festivals around Europe” was a high point, he says proudly, “especially cos I’m travelling with all my friends and family … I’d spend half the booking fee on bringing people with me.”
Rap is unlike most careers. Many rappers start in their earliest teenage years, freestyling with friends or on camera, moulding their realities into words. Those of Nines’ generation followed this path, part of a culture threaded through Black and working-class communities across the country, the urge to pull lyrics out of the ether as standard as football and religion.
“I’ve always been rapping,” he says, “for as long as I can remember.” There are clips of him at 17, rapping on early street DVDs. Boys crowd round a camera as a young Nines, a chain dangling from his neck, recites lyrics about being stuck in the daily grind and having friends in prison.
But his life has moved on from where we first met him at 17 years old, dreaming of escape. The decision to retire is a reflection of this, a new chapter of his life opening as another slips away. His weekends consist of spending time with his daughters or working on the album, his reality slowly drifting away from the one portrayed in punchline-heavy street raps.
“People are like: ‘I want old Nines,’” he says, but “I’m not 22 no more. I live a different life.” He continues: “It’s deeper than me. Even with the title of the album, you know how many people from jail have called and said: ‘Bro, I wish I quit while I was ahead’? It’s deep. Man’s almost a blueprint for street guys.”
The album has a sense of things coming full circle. Among the most notable examples of that comes on Don’t Cry. Nines’ older brother Wayne, also known as Zino, was killed in 2008. In the years that have followed, Nines has kept his memory alive through tributes in song titles and in the name of his label, Zino Records. On Don’t Cry, Zino, who also made music, joins him on record, his voice floating through the chorus in a posthumous sample from an old song. His cousin Begee is also featured. “I’ve already been to hell and back when Zino died,” Nines raps poignantly.
Freedom and escape have long run deep in the undercurrents of his music, a desire to cut loose from the trappings of his environment and lifestyle. “One day I’m gonna blow and put my team on the map,” he rapped on his first mixtape, From Church Road to Hollywood, in 2011. “Leave the game. Won’t have to buss guns or sell keys of caine.”
His life bears out these songs. Nine was raised on the Church End estate in north-west London, a place many refer to simply as Church Road. In a previous interview in 2020, we walked through the estate and he spoke of growing up too fast. “I was stood on the corner at 15,” he said then, “and stay trapping because I was always like: ‘Blud, I need to get out of this shit one day.’ Financial freedom.” His lyrics at times sketch vivid portraits of money made by illicit means, of violence and addiction and street hustling, young lives drifting down dark roads.
His rap career has diarised this tug between the streets and a legitimate livelihood. In 2013, he was charged with intent to supply cannabis and sentenced to 18 months, spending five months incarcerated. When he was released, and his music continued to spread across the country, he was managed briefly by the late Jamal Edwards. A new world beyond Church Road was opening out ahead.
But by the autumn of 2021, he was back inside, sentenced to 28 months for a plot to import 28kg of cannabis from Spain and Poland. “The first time I deffo didn’t learn my lesson, I guess,” he says.
He was 31, one of the most popular rappers on the continent, had videos with millions of views, had been nominated for Brit awards and had walked out Anthony Joshua at Wembley stadium. And despite it all, he was in prison. That second stint was the hardest he says. Phone conversations with his daughter were “burning my heart”. On the phone she would ask: ‘When you coming home, Dad?’ he says, “and I’m lying like. ‘I’m in Dubai’ and shit. That was hard, man.”
There were also difficult days in court. He remembers looking out at his mum, his auntie and his grandma, thinking how these same three family members had all gathered here for him decades ago when he was a teenager. “I was like 16 and they looked so young,” he says. But now, this time round “My mum and my auntie look like my gran’s age, and my gran looks mad old, and I’m picturing them with that same sad face and it’s like: ‘I can’t believe I’m doing this to them.’ I can’t believe I’m letting them down at that age, so that was it. That was enough for me.”
After serving six months, he was released, and moved his life fully above board. There was pressure at times, no fallback now if music didn’t work out. “It was always fun until Crabs in a Bucket,” he says, “then there became too much on the line I guess.”
But among it were signs to stay the course, such as the time his older brother was talking about someone from the local area and said: “Anyone that goes jail for the same thing twice is a fool.” The statement struck home. “He was talking about someone else, but I’ve been jail for the same thing twice so it’s like he was talking to me.” The day after, he got booked for Wireless festival.
The change was also forced on him. After being released “I was [banned] from being in Church Road or around,” he says. There was a list of 50 or so people he was prohibited from associating with, many of whom were his old friends. The area he grew up in, the small world his music had bloomed into colour, the faces, people and roads given life on his mixtapes and albums now existed at a remove. But they remain in his songs, in this album, a local history carved into music.
Rap will likely stay present in his life in small ways, he says, freestyling by himself in the car when an instrumental plays through the speakers, or through unreleased songs soundtracking the films he plans to release, or perhaps an attempt at ghost-writing for other artists too. But as a recording artist, he says his career is over. The magnitude of stepping away from the craft he has practised since he was a boy is still sinking in.
“Of course I’m going to miss it,” he says, “And it probably ain’t even hit me yet. I think when I do the O2 and it’s over, I’ll probably be staring around like, ‘Oh shit it’s really done.’ But yeah man, evolution.”
Quit While You’re Ahead is out now on Zino Records.
