The 'High' hitmaker has a tendency to crowd surf at his festival shows, and once even attempted to do so through 50,000 people on a Union Jack inflatable boat, but even when doing stunts like that he says he never ends up looking "cool".
Speaking in an interview with the Daily Star newspaper's Wired column, he said: “I’d love to be cool but I’m never gonna get that title.
"The nearest I got to being cool was at Glastonbury and I was playing on the Pyramid Stage and I thought I’ll crowd surf.
“So I threw myself off the stage and I crowd surfed as the sun was going down at Glasto and I thought you know what, ‘I am cool, I am!’
“Then I went back to the stage and I realised it was too high for me to climb back on and there was a man on the stage and I looked into his face and said, ‘Help me’.
“I realised he was a BBC TV cameraman broadcasting to the nation. "Not cool, never going to be.”
The 45-year-old singer has developed a reputation for his amusing and sarcastic messages on Twitter, and James claims that his ability to not take the platform "too seriously" has helped him to maintain a healthy relationship with social media.
The 'You're Beautiful' hitmaker - who has 1.8 million followers on Twitter - previously explained: "I don't really care about it so much. I just think that humans should be kind to each other and treat each other nicer.
"But on social media, some people don't. So, I laugh to myself when I'm reading them, and don't take them too seriously."
Meanwhile, the 'Goodbye My Lover' hitmaker recently opened up about the great deal of "loneliness" he feels when he's touring the world without his wife and young son.
James penned the track 'Cold' for his upcoming album 'Once Upon A Mind' about "the ocean between" him and Sofia Wellesley - who he tied the knot with in 2014 - and their three-year-old boy, whose name they are keeping private, when he's playing across the pond and how hard it is for his family and him to be apart for such long periods.
He said: “I have a young family, I have a wife who I leave at home for extended periods of time while I’m away on tour and all of that has an impact of loneliness for me while I’m away on tour and a huge responsibility for those I leave behind.
“If I am touring in America as I constantly do for months on end there is an ocean between us physically as well as metaphorically.”