The reason the portrait of Winston Churchill looks grumpy on the… The reason the portrait of Winston Churchill looks grumpy on the £5 note, is because the photographer had just snatched the cigar out of Churchill’s mouth.Source: Weird Facts Interesting Facts Related posts:Winston Churchill – WTF fun facts Winston Churchill – WTF fun fact Gangster Winston Churchill – WTF fun facts Picasso’s self portrait age 15 vs self-portrait age 90.