25. Tony Hawk
One of the easiest ways for a celeb to be funny and relate to fans is by showing the everyday/normal people shit they go through. Tony Hawk's tweets are one of the best examples of this on Twitter. You won't find the retired pro skater talking about the millions of dollars he's made or that time he landed a 900 when the cameras weren't around. Instead, he's talking about mischief his kids get into, coming across horse shit that's on sale for a dollar, and discussing testicles in a recent interview.