Today is September 14, 2023, and on this day, 40 years ago, Amy Winehouse was born. Despite her brief career, Amy will always be remembered for her trailblazing records and powerhouse performances. Ones that immediately spring to mind are this 2008 Grammys performance, beamed live from London to the ceremony in LA, and this early career knockout on Jools Holland from ‘03.

Although there are a plethora of iconic live performances and musical moments to choose from when it comes to Amy, one other thing she’ll always be remembered for is her wicked sense of humour. So, to wish her a happy 40th birthday, we count down all the hilarious non-musical moments of Miss Winehouse’s career, the best interview clips and TV skits that remind us why she truly was one of the best to ever do it.

BABY AMY

In this early interview with Jonathan Ross, the host asks a 20-year-old Amy if people in the industry have tried to change her. “Yeah”, she replies, “one of them tried to mould me into a big triangle shape, and I went: nooo.” During the interview Amy shows an emotional depth far beyond her years, and is truly a pleasure to watch – make sure you take a look at the whole thing, plus her mesmerising performance of Frank cut “I Heard Love Is Blind” at the end.

FAN-GIRLING OVER BEYONCÉ

As she was running late for the 2004 Brits, a reporter grabbed Amy on the carpet to ask her a few questions. “I’m really late… I don’t wanna miss Beyonce!!” she says of the Destiny’s Child star, who was performing “Crazy In Love” at the ceremony. It’s only a short clip, but it’s a heartwarming snapshot of the singer during her Frank album era: nervous, excitable, and beaming ear-to-ear, excited for what the night might bring.

VOTE FOR AMY

In 2004, Amy was nominated for Best Female Solo Artist at the Brit Awards, up against Jamelia, Annie Lennox, Dido and Sophie Ellis Bextor. Amy kicked off her makeshift campaign with Simon Amstell on Channel 4’s Popworld, driving around London in a silver Nissan Micra, screaming at random people on the street through a megaphone.

Highlights include Amstell telling strangers that Dido likes hurting small animals (disclaimer: she does not) and Amy throwing rocks at a billboard for Dido’s album. She then goes on to shout out the window of the car, “DON’T VOTE FOR DIDO. DIDO WILL KILL YOU”. But that wouldn’t be Amy’s only run-in with the “Stan” singer that year…

DIDON’T

In March 2004, a month after losing the Brit award to Dido, Amy was asked about her in an interview. “Look at Dido, she used that album to clean out her emotional closet,” says the clueless interviewer. Amy’s bored response (“Did she?”), coupled with multiple eye rolls and a pick at her lip shows just how disinterested she is, but the interviewer keeps banging on. “It’s all about the break up of her relationship… and the whole thing about not going down with the ship,” she continues, a reference to Dido’s song “White Flag”. Dido’s ship might not have been going down, but this interview was – Amy emitting the heaviest sigh recorded in modern media was a testament to that.

PISCES = GAY BOY

A clip from her 2007 concert film I Told You I Was Trouble saw Amy and 00s TV stalwart Alex Zane in a record shop, thumbing through the sleeves. “When’s your birthday?” Zane asks, and Amy tells him it’s on September 14. “Virgo,” he says in response. Amy then asks, “When’s yours?” and Zane replies “March the third,” to which Amy immediately responds “gay boy”. Is it childish? Yes. Do we care? Certainly not. Plus, a March birthday is a little sus if you ask me…

A GAY SEX SYMBOL

If you thought Amy’s quip at Alex Zane was a tad homophobic, then this next interview will put your thoughts to rest. In a 2007 outing with Kelly Osbourne, Amy was asked if she considered herself a sex symbol, to which she replied, “only to gays.”. The same clip is filled with other hilarious moments, like when she calls Alice Cooper her favourite female singer, or when she insists she only gets treated differently as a female artist “when I’m on my period”.

JUSTIN TIMBERLAME

This moment from the 2008 Grammy’s wasn’t actually included in the broadcast, but only came to light years after. Amy wasn’t at the LA event, but beaming in via video from London, and as the nominations for Record of the Year were read out, the camera caught her reaction.

“His album’s called What Goes Around Comes Around?” she asks incredulously of Justin Timberlake’s nomination. The moment’s great for two reasons: the face that Amy makes straight after when she realises she’s been caught is priceless, but the fact that she’d not even heard of Timberlake’s track – a huge song that was inescapable at the time – just shows how she was never putting on a front. Justin Timberlake? Sorry, who is he?

PIECE OF SHIT VS FIT

When she came off stage after her 2008 Brit Awards performance of “Love Is A Losing Game”, Denise Van Outen chased Amy down with mic in hand, asking her how it went. “I enjoyed it, it was a bit shit though,” replied Amy in her classically blunt way. When Van Outen tells her to be kinder to herself, Amy insists, “It was a piece of shit, you look fit though” before turning round and walking off. Despite Amy's insistence that her performance was shit (it wasn’t), we love how she just couldn’t resist telling Van Outen how hot she looked (she did). Women supporting women!!

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