The Clybourn name originated in 1917 at this street’s northern terminus (near Roscoe) and slowly worked its way down. That first bit was originally called Foothill Avenue and was presumably rechristened to avoid conflicts with other Foothill-named streets. My guess is that some civil engineer took inspiration from Chicago’s Clybourn Avenue, a diagonal thoroughfare that was mentioned often enough in the Los Angeles press. That Clybourn was named for Archibald Clybourn (1802-1872), one of the Windy City’s earliest residents. Archibald’s son Henry (1842-1913) did live in L.A. during his final years, but there’s no indication that he would have inspired this street name.