The song's titular character is a tall man from the
South Side of
Chicago whose size, attitude, and tendency to carry weapons have given him a reputation for which he is adored by women and feared and respected by men. He is said to dress in fancy clothes and wear diamond rings, and to own a custom
Lincoln Continental and a
Cadillac Eldorado, implying he has a lot of money. He is also known to carry a
.32 caliber handgun in his pocket and a razor in his shoe (shown in the music video as an old-fashioned
straight razor). One day in a bar he makes a pass at a pretty married woman named Doris, whose jealous husband engages Brown in a fight. Leroy loses badly and is described as looking "like a jigsaw puzzle with a couple of pieces gone". The story of a widely feared man being bested in a fight is similar to that of Croce's earlier song "
You Don't Mess Around with Jim".
Cash Box described it as "a delightful new single in the same musical vein as his 'You Don't Mess Around with Jim' smash that started his career".
Record World called it "another story-song similar to the one that started it all for [Croce], 'You Don't Mess Around With Jim. ==Inspiration==