The name Waylon is a boy's name of English origin meaning "land beside the road". Waylon is ranked #162 on our popularity charts and is often added to lists like Boy Baby Names Moving Up Fast and discussed in our forums with posts like "Picky Parents - Sibsets Version".
From the experts:
Country singer Waylon Jennings bestowed a kind of outlaw image on his name. However, for many children of the 1980s and '90s, Waylon will be forever associated with The Simpson's character, Waylon Smithers.
Waylon Jennings' son, also named Waylon, is called Shooter, and Shooter's young son Waylon Albert with actress wife Drea DeMatteo will be addressed as Blackjack. Grandpa Jennings was originally called Wayland, but the name was changed early on by his mother.