U2 have reportedly attempted to sell their shares in Live Nation after the value plummeted to just over a fifth of the original amount.
The Irish band signed a deal with Live Nation last March that tied them in for 12 years with the band being paid partly with stock.
U2 were given 1.6 million shares with Live Nation guaranteeing that they would be worth $25 million, when the market closed on Wednesday evening in New York they were worth just $6.1 million.
According to the Wall Street Journal Live Nation were they forced to make up the remaining $19 million, in an SEC filing Live Nation said they would do this with cash on hand or borrowed money.
Live Nation last year signed similar deals with Madonna, Jay-Z, Nickelback and Shakira – promising to pay out millions to artists in return for revenue from the 360 deals which encompassed concerts, fanclubs and merchandise.
Live Nation have moved to play down the U2 stock sale, with Chief Executive Micahel Rapino saying: "Madonna and U2 are the only two deals that did contain this provision. The Madonna business is great, and we look forward to monetizing our investment in U2 next year."
U2 are set to tour in 2009 with announcement expected to be made in market about the schedule.