I bet you think this song is about you, don’t you, don’t you, don’t you…

50 years ago today, You’re So Vain was sitting on top of the US Billboard chart. 

Since its release in November 1972, few songs have been subjected to as much scrutiny. Just who was Carly Simon singing about? The identity - or identities - of the cad who had one eye in the mirror as he watched himself gavotte remains hotly debated to this day. 

The concept of ‘diss’ songs was popularised by hip hop artists, but singer-songwriter Simon’s takedown remains among the most scathing to be committed to record. 

While the lyrics comprehensively flay the song’s subject (or subjects), her takedown is delivered with class and restraint. 

It’s hard to say the same of No Vaseline, gangsta rapper Ice Cube’s visceral 1991 attack on his former NWA bandmates and their manager Jerry Heller. To say its homophobic and antisemitic slurs have aged badly would be a considerable understatement, but its blows were simply too devastating for the group to respond to. 

Since then, the genre has seen numerous high-profile beefs, occasionally with deadly consequences. Vicious insults set to music, however, predate even the tale of that man who walked into the party like he was walking onto a yacht. 

We’ve taken a look at some of the all-time greatest insult songs.  


The title track of this album is often voted the greatest song of all time, with its lyrics promoting ideals of peace, love and understanding. 

Track eight was somewhat less wholesome. 

Following the acrimonious breakup of the Beatles, Paul McCartney took digs at Lennon and Yoko Ono on August 1971’s Too Many People, which contained the lines “you took your lucky break and broke it in two” and “too many people preaching practices”. 

Lennon responded with How Do You Sleep?, which was far less subtle in its jabs. Referring to a famous Beatles conspiracy theory and McCartney’s most beloved song, he sings “those freaks was right when they said you was dead” and “the only thing you done was yesterday”. 

The world’s most famous songwriting duo would go on to patch up their friendship, but neither man came out of this episode with their reputation enhanced.

CARLY SIMON - YOU’RE SO VAIN (No Secrets, 1972)

In August 2003, NBC Sports president Dick Ebersol bid $50,000 to find out the subject of You’re So Vain, but it appears that the song may be about more than one man. 

In November 2015, she confirmed that the second verse is about Bonnie and Clyde star Warren Beatty, but told the BBC: “Now, that doesn’t mean that the other two verses aren’t also about Warren. It just means that the second one is."


A high point on one of the best-selling albums of all time, Go Your Own Way arose from a period of internal strife. With Christine and John McVie separating, Lindsay Buckingham and Stevie Nicks were also breaking up. It was the latter whose relationship provides the lyrical inspiration here, with Buckingham admitting that “loving you isn’t the right thing to do” and go on to claim “packing up, shacking up is all you want to do”. 

Speaking on the Song Exploder podcast, Buckingham explained: “I sort of was coming to terms with the fact that I may not be over this person and, at the same time, I’m aware that I’ve got to accept what’s happened and move on. 

“I don’t think there was ever any worry in my mind about trying to mask who I might have been talking about.”

Nicks told Rolling Stone: “it was like, ‘I’ll make you suffer for leaving me’. And I did.”

READ MORE: 10 Bruce Springsteen songs that tell the rock legend's story


Long before Biggie v Tupac, there was Boogie Down Productions v the Juice Crew. The Bridge Wars kicked off in 1985 when the Juice Crew’s Marley Marl and MC Shan released The Bridge, which was interpreted by some as a claim that hip hop was born in Queensbridge. 

BDP’s DJ Scott La Rock and KRS-One took issue with that idea on South Bronx, with KRS-One rapping: “So you think that hip hop had its start out in Queensbridge/If you pop that junk up in the Bronx you might not live”. 

Shan and KRS-One traded further blows on the former’s Kill That Noise and the latter’s The Bridge Is Over, with KRS-One and BDP widely viewed as the winners of the conflict.


Only You’re So Vain has generated more debate as to the identity of the man being sung about. While Carly SImon’s delivery was restrained, Morissette delivers a cathartic howl of retribution. 

Who was the “Mr Duplicity” who “told me you’d hold me until you died”? The likes of Friends star Matt Le Blanc have been mentioned, but actor and comedian Dave Coulier has suggested that the song is about their two-year relationship in the early ‘90s. 

The mystery featured in a 2002 episode of HBO comedy Curb Your Enthusiasm in which Morissette made a cameo, but the Canadian singer has to this day refused to reveal just who she hated to bug in the middle of dinner. 

2PAC FT. OUTLAWZ - HIT ‘EM UP ((Death Row Greatest Hits, 1996)

The sheer venom and ferocity of this diss track might even have given Ice Cube pause for thought. 

Having at one point been friends, the feud between Biggie ‘Notorious B.I.G.’ Smalls and Tupac ‘2Pac’ Shakur embodied rap’s East Coast-West Coast beef. After Tupac was shot while resisting a robbery in 1994, he suspected the involvement of Biggie and his manager Puff Daddy. Those suspicions were heightened after Biggie recorded Who Shot Ya?, and Tupac got to work on one of the most blistering recordings in rap history.

Joined by his group Outlawz, Tupac takes aim at Biggie and everyone close to the Brooklyn rapper for five relentless minutes. “Who shot me, but you punks didn’t finish/now you ‘bout to feel the wrath of a menace” might be the only line that could possibly be quoted in this newspaper. 

Within four months of the song’s release, Tupac was the victim of a drive-by shooting. Six months later, Biggie met the same end.

LAURYN HILL - LOST ONES (The Miseducation of Lauryn Hill, 1998)

25 years on, The Miseducation of Lauryn Hill remains a landmark album. Having risen to fame as the frontwoman of hip-hop trio The Fugees, Hill mixed potent rhymes with soulful vocals on what remains her only solo studio album. 

Lost Ones has been perceived as a swipe at her former Fugees bandmate Wyclef Jean, with whom she had at one time been in a romantic relationship. Lines such as “A groupie call, you call from temptation/Now you want to ball over separation/Tarnish my image in your conversation” left no doubt as to what Hill made of his behaviour. 

NAS - ETHER (Stillmatic, 2001)

Jay-Z v Nas was rap’s most high-profile beef since Biggie and Tupac, and reached new heights in September 2001 when the former released Takeover. Over a dramatic sample of Five to One by The Doors, Jay-Z referred to the widely-held belief that Nas’ output had significantly decreased in quality since 1994’s classic Illmatic record, accusing him of having a “one hot album every ten-year average”. 

A gauntlet was laid down, and three months later Nas responded with the vicious Ether. When the song isn’t mocking Jay-Z’s appearance, he’s claiming the future Mr. Beyonce was outrapped on his own song by Eminem.

Ether’s ugly barrage of homophobic slurs makes it an uncomfortable listen in 2023, and underlines how much of gangsta rap’s golden age feels like a relic in the age of Lil Nas X. 

Jay-Z countered with Super Ugly, a song containing blows so low it led his own mother to call the Hot 97 hip hop radio station and demand he apologise to Nas and his family. 

Nas was hailed the winner of the feud, but the two would later put the rivalry behind them. Jay-Z welcomed Nas onstage in 2005 and declared: “All that beef s*** is done, we had our fun. Let’s get this money.”


Any chance of Cry Me A River’s lyrics being overshadowed by Timbaland’s futuristic production disappeared upon the release of the accompanying video, in which Timberlake appears to stalk a lookalike of ex-girlfriend Britney Spears.

2003’s Everytime is believed to be Britney’s response, but that song contains nothing as spiteful as Timberlake’s “Now it’s your turn to cry, so cry me a river”. 

READ MORE: 30 great Later... with Jools Holland appearances on show's 30th anniversary

MARTHA WAINWRIGHT - BLOODY MOTHER F***ING ASSHOLE (Bloody Mother F***ing Asshole, 2005)

Cult singer-songwriter Loudon Wainwright III, who wrote the song Rufus Is A Tit Man about his son breastfeeding, paid the price for discussing family matters in song. 

With Rufus having already grown up and established himself as an acclaimed songwriter, his sister Martha joined the family business with this sharp riposte to her father. 

Speaking to the Guardian, she explained: “For most of my childhood, Loudon talked to me in song, which is a bit of a s****y thing to do. Especially as he always makes himself come across as funny and charming while the rest of us seem like whining victims, and we can’t tell our side of the story. 

“As a result, he has a daughter who smokes and drinks too much, and writes songs with titles like Bloody Mother F***ing Asshole.”



“You can wag your tail, but I ain’t gonna feed you no more” insists the blues and R&B singer, dressing down a man who falsely claimed to be high class. 

This original version turns 70 next month, but many will be familiar with a cover performed by some bloke from Memphis.

BOB DYLAN - POSITIVELY 4TH STREET (Positively 4th Street, 1965)

Sharing the organ sound of Dylan’s lauded Like A Rolling Stone, these lyrics were every bit as withering as those of its predecessor. 

There has been much speculation as to who had “a lot of nerve to say you are my friend”, but the consensus appears to be that it was a broadside against the residents of New York’s Greenwich Village who took issue with folk singer Dylan going electric.


Lyrics such as “Yeah you know her, ‘Miss Groupie Supreme’” and “her nose job is real atomic” suggest a personal vendetta on Debbie Harry’s part, but Blondie’s frontwoman was actually sending up the manner in which female musicians of the punk era - including herself - were discussed. 

In 1999, she told BBC Radio 2 that the song was about media intrusion and how gossip columns cover women.

JOHN COOPER CLARKE - TWAT (Snap, Crackle & Bop, 1980)

Print off Twat’s lyrics and put on a blindfold, and wherever your finger lands there will be a classic insult. 

The punk poet sets the tone with “Like a nightclub in the morning, you’re the bitter end/Like a recently disinfected s***house you’re clean round the bend”, and wraps things up neatly with “What kind of creature bore you, was it some kind of bat?/They can’t find a good word for you, but I can…Twat”. 

ARCTIC MONKEYS - BRIANSTORM (Favourite Worst Nightmare, 2007)

Arctic Monkeys frontman Alex Turner has spoken repeatedly of his admiration for John Cooper Clarke, and the band even covered his song I Wanna Be Yours in 2013. 

Clarke’s influence is clear on the opening track from their second album, with Turner mocking a poseur with a t-shirt and tie combination which he couldn’t take his eyes off.

READ MORE: Arctic Monkeys, Taylor Swift and 70 classic number two hits

He later told the NME that they had met Brian backstage in Tokyo, and explained: “when he left the room, we were a bit in awe of his presence. So we did a brainstorm for what he was like, drew a little picture and wrote things about him.


(Contains explicit lyrics, including homophobic slurs in Ether by Nas)