Madonna’s interview with David Letterman in 1994 is still excruciatingly awkward three decades later. The sit-down conversation went down in TV history after Madonna said f**k fourteen times – making it the most censored US network talk show ever. Throughout the chat, the La Isla Bonita singer, then aged 34, chugged on a cigar, doled out insults – and even produced a pair of her own knickers.

Her behaviour outraged audiences – who complained in their droves to watchdog the Federal Communications Commission. Critics also blasted Madonna, now 65, with The New Paper stating at the time the general consensus was that she had reached the ‘lowest low.’ Let’s look at all the controversial moments from the March 31, 1994 episode of Late Show with David Letterman featuring Madonna.

Letterman urges Madonna to kiss an audience member At the start of the interview, Letterman, then aged 47, told Madonna to kiss a guy in the audience on the forehead as it would ‘knock him out.’ Respectfully declining the bizarre invitation, Madonna stayed firmly put in her seat and responded: ‘I can’t.’ Letterman then praised the Material Girl for not caving in to peer pressure.

Madonna tells Letterman to smell her underwear If you thought telling someone to snog a stranger was weird, well, Madonna arguably gets a whole lot weirder. It appeared the Vogue singer had gifted a pair of her own knickers to Letterman for his, er, personal consumption. After noticing her pants discarded on.