“Awkward”: the night Prince felt compelled to save Amy Winehouse from destruction
One night in 2005, Amy Winehouse stumbled into a pub in Camden and laid eyes on someone for the first time. Blake Fielder-Civil didn’t just captivate her immediately—he introduced her to a new kind of romance, one that set her heart and soul on fire and inked her mind and skin with promises of passion and safety. The only downfall of this meet-cute was that, while it ignited her life in ways she never knew possible, it left others wondering if she had flown too close to the sun.
Nothing would ever be easy with Winehouse’s heart involved. Following the pair’s brief split, the singer channelled her heartbreak into Back to Black, comparing the breakup to things like “fuckery” and a “losing game” before fate brought them together again in 2007. They eloped before the harsh eye of the media, which made its position on the entire matter clear—Winehouse was the victim.
During the same year, Winehouse was invited to perform alongside Prince for the final date of his residency at London’s O2 arena for a duet of her heartfelt ‘Love Is A Losing Game’. Performing Back to Black songs in this capacity felt like something of a prophecy, particularly as the pair continued to live out their tumultuous relationship in the spotlight, with many wondering why she still gave Fielder-Civil the time of day.
This held lasting prominence with Winehouse singing about love being a game she “wished I never played”, with Prince beside her like a fleeting presence, invited for one moment into the chaos that had long defined her love life. However, although privy to the context of her life at this particular juncture, Prince’s suspicions were confirmed when the pair went backstage, Fielder-Civil taking the opportunity to rob some money from him in the name of fun.
One of Winehouse’s longtime friends, Tyler James, recalled these events in his book My Amy: The Life We Shared. He described how Prince’s videographer Phil Griffin (who hadn’t worked with the star for long) became unknowingly framed as the villain when Fielder-Civil stole some money from his dressing room after the show. According to James, Fielder-Civil’s presence changed the entire atmosphere, making everyone suddenly feel “edgy”.
“There was cash in the dressing room, just lying there, out in the open, on the makeup table. No one was paying attention to it,” he wrote. Afterwards, Fielder-Civil allegedly joked about taking “hundreds of pounds”, which Winehouse “brushed off”. He said that she knew it was “wrong” but that she felt “awkward”, so she laughed about it instead. “It turned out Blake stole some of Prince’s hairbrushes, too,” he added.
According to James, Prince’s team had discovered it was missing and immediately accused and fired Griffin, who was subsequently “beaten up and turfed out the 02.” When Winehouse called Prince the following day to apologise and tell him she would return the money, he apparently said he didn’t care and that all he worried about was her safety, offering to “spirit” her away so that she would be free from Fielder-Civil.
While her liaison with him would eventually come to an end, the relationship undoubtedly left Winehouse charred in countless ways, the least of which was her fatal addiction to substance abuse and inability to commit to any sort of drug or mental health rehabilitation. Prince and many others might have detected the destructive path she was already on, but the only person who could have saved her from herself was her.
