In the World War II era, Roger had nothing but the most positive associations, actually used by military personnel to mean 'Received and understood'--or A-OK, and though it is now on extended furlough, it does have a long and distinguished history. Introduced to England after the Norman Conquest of 1066, Roger soon became very popular there, with nicknames Hodge and Dodge, and had a long run later in the U.S, remaining in the Top 100 for 55 years. Right now it ranks at Number 558.
Roger has an impressive list of notable namesakes, both fictional and real. Roger Chillingworth is a major character in Hawthorne's classic The Scarlet Letter, and the name appears in works by Ben Jonson and Anthony Trollope. In sports, there have been Rogers Maris, Clemens, Bannister and Federer, in entertainment actor Roger Moore and Roger Daltry, lead singer of The Who.
On the dark side, there is the Jolly Roger--a pirate's black flag with skull and crossbones--which a little boy might actually love.