Pop star and former X Factor judge Gary Barlow and two other Take That members must pay back millions of pound in tax after a court ruling.
Tax judge Colin Bishopp ruled that the former boy band members were part of a huge tax avoidance scheme.
Barlow and Take That bandmates Howard Donald and Mark Owen paid £66 million into two partnerships that appeared to be music industry investment schemes but were artificial tax shelters for the rich.
The scheme allowed the musicians to avoid tax on around £63m from world tours and CD sales.
Judge Bishopp rejected the explanation that more than 50 partnerships, set up by a company called Icebreaker Management, had been set up for commercial purposes.
"Icebreaker is, and was known and understood by all concerned to be, a tax avoidance scheme," he said.
"The aim was to secure [tax] relief for members, and to inflate the scale of the relief by unnecessary borrowing."
The business affairs of Barlow, Donald and Owen have been called into question before. In 2012 it was reported that they sheltered about £6.5m in a "highly aggressive" Jersey-based tax scheme called Liberty.
The three band members have not commented since the latest ruling. In 2012 their lawyers said the stars paid significant tax and did not believe they were investing in avoidance schemes.
The former X Factor judge is worth £60m, according to the Sunday Times Rich List 2013.
As the chief songwriter for the original Take That, Barlow received a higher proportion of the band's income than the other members.
Take That had eight No 1 singles and sold over 15 million albums worldwide between 1992 and 1996, earning £80m.
A six-time Ivor Novello Award recipient, Gary Barlow has sold over 45 million records worldwide with Take That.
Barlow received an OBE in 2012 for services to music and charity.
Watch Gary Barlow singing Take That's Rule The World on the X Factor