Flash forward many years later and Oseary said he reconnected with Prince, with whom he'd become friendly. "I called him a few years back with the idea of @Madonna and Prince going on tour together," Oseary wrote in a lengthy Instagram post. "I pitched it to Madonna and within a second she said 'I like it, we can call it the Royalty Tour... The Queen and The Prince'.... I love the way she thinks... When I told Prince the idea he said: 'the world isn't ready for this, it's too big.'"
The hook-up made sense, and not only because the pair were two of the most pioneering video music artists of all time, practically helping to invent the genre (along with Michael Jackson) in the 1980s. Prince appeared twice on Madonna's 1989 album Like a Prayer, on the distorted guitar into to the title track, as well as on the duet "Love Song."
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Despite Prince's shut-down of the idea, Oseary said he always thought he might still pull off the double bill one day. "@Madonna performed in #stpaul last year and Prince was generous enough to host us and perform for us after that show at his home #paisleypark," he recalled. "He didn't go on stage until 3am, and per usual the show performance was mindblowing.. He joined me this last New Years in St Bart's and performed for my friends party at what will now be the last time I saw him.. It's the one and only time I was able to actually work with him directly.. I won't forget that electrifying performance.. Or the smile on his face that night.. And the love that he gave me."
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Oseary said Prince always treated him kindly, even if they didn't always agree and they sometimes argued for hours. "But he understood that I respected him dearly and cared for him," he wrote. "I tried my best to help him on record business matters.. And even in his passing I'm here to help.. I would have done anything I could and wish I achieved more for him on his very clear issues.. The man had the strongest of opinions on contracts and on artists rights."
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The post was accompanied by a photo taken in the summer of 1999, in which Oseary is seated next to a chatty Madonna, who is right next to fashion icon Donatella Versace. On the far end of the table is Prince, who Guy clearly has his eyes locked on. "I have the original lyrics to 'purple rain' on my wall and I was always too embarrassed to tell him," he said. "Maybe he would think I was crazy for paying so much years back for those lyrics or maybe he would just take it off my wall and say 'thank you, I was looking for this'... Who would stop him?.. Not me.. Today not only will doves cry, we all cry.. You will be missed.. I love you.. Rest in peace."
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Here's the full post: