Pitbull @ Roundhay Festival
Some artists see success overnight. Some only add their names to the record for future generations. An elite, hairless few are capable of it all. Jon Dell and 70,000 others meet Mr Worldwide.
The last time Pitbull had a solo single that charted in the UK was 2015, where Fun (feat. Chris Brown; yikes) peaked at number 68. For all intents and purposes, Pitbull is merely a heritage act at this point, but on a sunny Friday afternoon among 70,000 others in Leeds’s Roundhay Park I stand, eyes bright and baldcap sweaty, abuzz with excitement like we are waiting for Michael Jackson in his 80s heyday. Coincidently, Michael Jackson played Roundhay Park in 1988 and 1992, which was probably how Roundhay Festival managed to convince Mr Worldwide to come to Leeds in the first place.
A heritage act, yes, but this crowd tells us that heritage matters. Of course it does. When an artist of an exceptional talent arrives, we as the consumer public must pay heed to their output, and ensure it remains for posterity. There is a reason why Shakespeare is taught in schools to this day. His last play was written over 400 years before Fun hit the airwaves.
In Leeds, alongside our stunningly bald headliner comes support from Jason Derulo, Tinie Tempah, and Lil John. Not one of these has had a major hit in the UK for several years, but somehow it’s my second time seeing Jason Derulo in 2026 (the first time was genuinely pretty incredible) and it’s also my second time seeing Pitbull himself (the first being in 2018, when he supported Britney Spears in Scarborough – the less said about that the better).
So what is it about them that attracts such an audience and hundreds of millions of streams? If we go back to the mid 2010s, we can sum up the popular music of the time in just one word: fun. The early 2010s was all about going out, getting wasted, having one night stands, and forgetting about it all tomorrow. Even if you were doing none of this, the music was there to do it all for you, uplifting and frivolous and spontaneous, and in a way that felt like it meant something. Even as music trends change, artists like Pitbull and Jason Derulo continue to attract millions of listeners because their songs are built around energy, familiarity, and hedonism. It’s music pitched to make people feel good, whether they're at a party, working out, driving, or simply looking for an upbeat soundtrack to their day, with a catchy chorus (or beat, or hook) that remains recognisable a decade or more later.
Nostalgia plays a major role in their lasting popularity, but on the night each performer is an undeniable tour de force. Real talents at what they do, singing, dancing, and with a roster of hits to back up the charisma. Throughout the evening (and in contrast to many contemporary stars) stage presence and bravado take priority over earnestness and sincerity. Songs such as Timber, Give Me Everything, Talk Dirty, and Want to Want Me might be tied to memorable moments from school, holidays, nights out, or special occasions, but in amongst the throngs of baldcaps, it’s banger after banger and it’s driving the crowd crazy. There is also just something intrinsically funny about 70,000 people singing along to Swalla – a Jason Derulo song that is essentially about his female partner swallowing the product of successful fellatio – at an ostensibly family-friendly event. It may be for good reason, but you just don’t get that any more in music.
For those few hours in Roundhay Park, the sheer joy and energy of the event made me forget about the emails I hadn’t answered, how tired I am by life, the guilt at not reaching out to a friend I really should check in with. For four consecutive acts, it was just happiness. Guilt-free and joyful. A mere week later, Pitbull would go on to scratch his name even deeper into the history books, an official Guinness World Record for the largest gathering of people wearing baldcaps. 22,000 in total, a mere fraction of the attendance at Roundhay. Real ones know the truth.
And in these dark times where we hurtle towards the end of the world, who doesn’t need a pick me up from Pitbull. You feeling depressed? Well, “Every day above ground is a great day, remember that.” Feeling lonely and like the world is out to get you? Well, “Believe me, been there, done that.” Do you need a flirtatious line for your other half? Well, what about “Your man just left, I'm the plumber tonight. I'll check yo pipes, oh, you the healthy type. Well, here goes some egg whites.” Shakespeare could never. ⚭
Jon DellPitbull was at Roundhay Festival, Leeds LS8, 3 July 2026
The I’m Back global tour runs in Europe and the US through December
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