Jessica Winter live at Headrow House review – life-affirming joy from a soon-to-be superstar

ArtistJessica Winter
VenueHeadrow House, Leeds
Date24 October 2025
OpenerAll I Ever Really Wanted
CloserL.O.V.E.
HighlightAll I Need
Undertone rating4/5

Unfazed by poor ticket sales, faulty lighting and a microphone mishap, on a rainy night in Leeds the Portsmouth upstart proved herself to be a hugely promising popstar. This show came packed with slick choreo, magnetic onstage charisma, versatile songs – and a thrilling Undertone first…

It feels like you can’t move for fantastic solo female pop these days. The first half of the 2020s has seen a fresh wave of exciting talent topping the charts – Sabrina Carpenter, Charli xcx, Chappell Roan, Olivia Rodrigo, Addison Rae and Lola Young to name a handful – each occupying their own niches and unique talents, impressively never treading on each other’s toes. In such a well-served, oversaturated genre, the talent (and luck) required to attain pop stardom these days is arguably higher than ever, at least for the women (as for the lads, their offerings of Benson Boone, Sombr and the guy that did Ordinary suggest their level of competition isn’t quite so Olympian). With so many niches covered – Charli’s brilliantly messy club pop, Roan’s Gaga-esque theatrics, Rodrigo’s bratty pop punk – is there any space left for any more pop upstarts hoping to see their own name in lights?

Enter Jessica Winter. The London-based newcomer (who has, in fact, been releasing music for over six years already) is one of few new hopefuls who genuinely does have the considerable talent required to hit the big leagues. Her recent debut album (unimaginatively titled My First Album) saw her emerge a fully-formed popstar with her trademark round glasses and messy-chic fringe, as well as a host of intelligently written and deliciously camp songs that range from feisty alt-rock to loved-up orchestral ballads.

The Leeds leg of Winter’s debut headline tour serves as something of a brutal popstar boot camp. It’s a blustery, dank night in the city with the gloom of November rapidly closing in, and more importantly this gig at the diminutive Headrow House has sold bafflingly poorly. There can’t be much more than 40 people in the room when Winter takes to stage; with the possible exception of Winter’s peer Phoebe Green in Newcastle, this might be the thinnest crowd at a gig I’ve ever seen. The muted response to the (admittedly lacklustre) support act MONK suggests that Winter might be in for a rough night.

But alas, great stars know that the show must go on regardless of the crowd size, and Winter rose to the challenge admirably with stomping opener All I Ever Really Wanted. Posing with the mic stand and eventually theatrically revealing her outfit under her trench coat (little more than a bra and some winningly ludicrous silk black gloves), it had the theatricality of an arena show, rather than a quiet pub in Leeds. Throw in some tasteful choreography with her one bandmate (who otherwise spent her time on backing vocals and pressing-play-on-a-laptop duties) and some heartwarming interactions with the handful of ecstatic fans in the front row, and soon the small crowd seemed to be having the time of their lives, all dancing and singing whenever they knew the words.

Winter’s fabulous charisma wouldn’t have had such an impact had her songs not been so exceptional. She’s early enough in her career not to have to worry about that obligatory quest to ‘find her own sound’, and instead she’s rightly content to experiment with a little bit of everything. Rowdy racket Got Something Good was a noisy delight, Winter and her bandmate emitting an almighty howl before an explosive, tightly choreographed finale. In fact, it gets so explosive Winter ends up accidentally throwing her microphone on the floor right at the climax of the last chorus. “Now that’s a mic drop!” she says afterwards with characteristic confidence. Feels Good (For Tonight), by contrast, is a catchy foray into throbbing house music, preceded by Only Lonely, a strikingly pretty ballad finished with a flourish from Winter on piano (the gloves, impressively, stay on). “Weren’t expecting that, were you?” she tells us after a graceful final arpeggio with a touch of well-earned cockiness.

It’s true that for the time being Winter wears her musical influences on her immaculate silk sleeves, but never does her music feel like a mere tribute to her pop predecessors. This evening’s cinematic closing number L.O.V.E. even comes with the obligatory Roan-esque letter-based dance moves and sports an orchestral finale very much in the vein of Bittersweet Symphony, but it’s also a rousing anthem about embracing yearning in its own right. “I want it all and more,” Winter sings, and judging by the spontaneous cheers from the audience, she’s not the only one getting wilfully swept away by desire.

That said, this gig’s highlight is clearly the camp techno number All I Need, which has Winter delivering a Vogue-ish chant over a spectacularly kooky synth riff. Halfway through the song, she starts inviting the most enthusiastic audience members up on stage, and before I know she’s offering me her gloved hand and for the first time ever I’m on stage at a gig I’m reviewing. The ensuing rave is pure, uninhibited joy, and as me and a stranger scream the faintly ludicrous lyrics at one another I’m reminded once again at the extraordinary power of music to bring people together. The experience was so enthralling it was only when I finally left stage that I realised that the stage lights had apparently broken, and Winter was left to close out the set in near darkness.

For the time being, Winter’s live show is hampered by a necessarily low budget, and switching from backing tracks to a live band is the obvious next step to add some much needed musical firepower. Nonetheless, the bits that money can’t buy – a captivating voice, a well-crafted persona, and conviction enough to show up to Headrow House with a wind machine and stage backdrop – are all very much present and correct. “’Cause she’s a big star / Don’t you believe her?” she sings tonight on her calling card Big Star, a Lily Allen-inflected romp broadly equivalent to Roan’s smash Pink Pony Club in its brave declaration of wild ambition (except this time the singer is trying to escape Portsmouth, not Tennessee). And I do believe her: mark my words, if Winter can keep this up, she’ll be our next national pop obsession in no time. You only have to watch one clip of Lady Gaga or Chappell Roan debuting their future hits to disinterested audiences to know that underattended gigs like these are the first step to stardom. If this dreary night in Leeds was a test of Winter’s credentials as a superstar of the future, she passed with flying colours.


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