16. John Daly
Career Years: 1987-Present
Career Lowlight: Passes out in front of a Hooters in 2008.
The colorful Daly is beloved by many for his antics on and off the course, but these antics are also likely the reason he has failed to become the star it looked like he surely would be after winning the 1991 PGA Championship. He has since waged very public battles with alcoholism and gambling addiction, and has also been married four times. These distractions have given him an almost larger than life persona. Although he does not have full playing privileges on the PGA Tour, Daly still gets invited to many tournaments because of how much the crowd loves his long drives, garish attire, and general belligerence on the course.