Waylon is a modern American form of Wayland, an English surname and place name usually explained as "land by the road", from the Old English weg and land; the spelling Waylon was made famous by country singer Waylon Jennings, who was born Wayland. The name has a strong country and western flavor as a result. Waylon ranked number 1082 in the United States in 2000, entered the top 1000 in 2002, rose from number 222 in 2015 into the top 100 in 2021 and reached number 56 among boys in 2025, its highest rank yet.