William Kennedy Smith

Unfortunately, photographs from the 1978 Salisbury School yearbook are hard to come by, so instead, we offer this photo of William Kennedy Smith boogying down with actress Brooke Shields in 1980 (and it is hard to imagine anything from a Connecticut prep school annual beating this for sheer weirdness).

Smith, an acquitted rape defendant, physician and reputed serial masher, holds the remarkable distinction of being one of the Kennedy family's most prolific black sheep. In the years since the controversial 1991 not guilty verdict in Florida, Dr. Smith has done little to validate the alleged wisdom of the jurors who let him off the hook.

In 1993 the busy doctor set aside his Hippocratic Oath just long enough to punch out a Chicago area bouncer, an offense to which he pleaded no contest. In 2004 Smith resigned from his humanitarian organization after an employee charged him with sexual harassment in a case that has since been dismissed (he later quietly returned to his post). Lurid details from another harassment complaint against the boss from hell leaked to the media in 2005, but by then this case had already been settled out of court. Dr. Smith's official online biography makes no mention of any of the preceding unpleasantness, but does note that he is the recipient of the coveted Scholl Recognition Award in Rehabilitation Research.