"Bad, Bad Leroy Brown" was a big hit for Jim Croce, who had a penchant for writing hit songs where somebody gets their butt kicked at the end (see: "You Don't Mess Around With Jim.") His 1973 smash reached #1 for two weeks that summer, a few months before the plane crash on September 20th of that year that took his life. The song was rated the #2 song of 1973 and nominated for two Grammy awards in the Pop Male Vocalist and Record of the Year categories. And it reinforced Chicago's South Side as a tough part of town.
Ol' Blue Eyes himself, Mr. Frank Sinatra, loved the song enough to cover it on his 1974 album Some Nice Things I've Missed, which was indeed releases on the pop charts that year. It made it only to #83.
Check out Frank Sinatra's cover here!
And just for good measure, here's Jim Croce performing "Bad Bad Leroy Brown" live on the old "Midnight Special" show back in 1973: