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As Adele signs a record deal with Sony worth £90m, here are four big-money tales of pop profit, loss and excess.

1. Robbie Williams

“I’m rich beyond my wildest dreams.” Thus the former Take That singer announced his £80m four-album deal with EMI in 2002, adding: “I’m going back now to count it all.” The contract was one of the first “360” deals, so called because they cover all aspects of a star’s earnings, from merchandise to sponsorship and endorsements. Such deals are said to favour the record company over the artist, but in this case it wasn’t a great deal for EMI: Williams subsequently entered a period of relative decline with poor-selling albums such as Rudebox (2006), and EMI itself was bought by Universal in 2012. Years later, Williams said he regretted the “wildest dreams” comment, describing it as “the most embarrassing thing I’ve ever done”.

2. Michael Jackson

For years rumours had been circulating that Michael Jackson was suffering financial difficulties; in 2003 he sued his former label Motown for unpaid royalties. Then came a deal — worth £200m — that could solve his problems. There was just one snag: when it was struck in 2010, Jackson had been dead for almost a year. The agreement, between Jackson’s estate and Sony Music Entertainment, was one of the biggest in music-business history, covering re-releases of mega-selling albums such as Off the Wall, unreleased material, DVDs, and a video game.

3. Happy Mondays

In 1992, the Manchester band were riding the crest of the “Madchester” wave when they were dispatched to Barbados to record their fourth album. Bad move. Once ensconced with their families in Eddy Grant’s home studio, members of the notoriously druggy band went off in search of narcotics. Singer Shaun Ryder and his brother Paul couldn’t find any heroin on the island, and settled for crack cocaine. Weeks went by, time and money ran short, and members of the band took to selling Grant’s furniture to fund their habits. They eventually returned with an album that featured no vocals. Their label, Factory, was already haemorrhaging money, and the cost of the sessions was among the factors that tipped the legendary label into bankruptcy.

4. U2

As record sales slump, pop acts have turned to touring as a way of boosting their fortunes and topping up their pension funds. U2 are the world’s most lucrative touring act — their 2009-11 “360°” tour grossed more than $736m in ticket sales. Not far behind in the touring charts are “heritage” acts such as The Rolling Stones, who grossed $558m for their 2005-07 tour, A Bigger Bang. But not all bands can be lured back together by the huge sums these tours can command: in 2007, The Smiths turned down a reported $75m from a consortium of promoters to tour. Singer Morrissey has always been firm on the matter: “I’d rather eat my own testicles, and that’s saying something for a vegetarian.”

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