Few who were there will ever forget it.
The night that rap legend Coolio strutted into Ayr was always set to be something a little different.
But when the music star hit the stage in the old Club de Mar wearing the black and white of Ayr United, a packed crowd went wild.
The Grammy-award winner, famed for his anthem 'Gangsta's Paradise,' was visiting Ayr in 2009 following a run on Celebrity Big Brother.
He stunned fans by performing his hit tracks while wearing a replica United shirt carrying his name on the back.
The top had been presented to him by the Ayrshire Post before his gig.
Reporter Stuart Wilson recalls: "When the guys at Club de Mar told us Coolio was coming to town, we couldn't wait to try something different.
"As a big Ayr fan, I suggested to the guys at Somerset Park that we get him decked out in the colours.
"Coolio couldn't have been more up for it. He came swaggering on stage with the shirt and was even pictured wearing it years later - so Ayr must have made a decent impression on him!"
The nighclub's management said: "The buzz created by Coolio was something else and people still talk that night all these years later.
"He was a real entertainer and it was a pleasure to have one of the great hip hop artists strut his stuff here."
Speaking to the Post on the night, Coolio said: "I come from the golden age of hip hop when all the greats came on the scene.
"There was serious competition around me at the time, but I was able to carve out my own niche.
"And at the end of the day, I think I’ll be recognised as one of the greats."
Coolio, who was 59 when he passed away, was found unresponsive on the bathroom floor of a friend's house in Los Angeles.
The exact cause of his death on Wednesday has not yet been revealed.
He began making music in the 1980s, but cemented his place in hip hop history when he recorded Gangsta's Paradise in 1995.
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