He represented the Netherlands with Ilse DeLange as part of the Common Linnets at the Eurovision Song Contest 2014, finishing in second place in the final.

Waylon started his career in 1995 singing in the television program Telekids where he sang the chorus of the song "Harry Stallion.

"[2] Since childhood he was inspired by country music and he played the drums with the band West Virginian Railroad.

A month later he received in a gold record for his debut album on the television program De Wereld Draait Door.

[9] He worked in Nashville and Hollywood on the album with, among others, Bruce Gaitsch, who previously wrote for Chicago and Madonna.

[10] In 2016, Waylon made a few appearances on talk show RTL Late Night; he lectured about the origins of pop-music and previewed tracks from his forthcoming album which came as a surprise.

He continued to explore his versatility by playing an annual concert-series in at the Rotterdam Ahoy in a joint venture with Radio Veronica's Top 1000 All Time Classics.

In June 2018, Waylon returned to RTL Late Night to perform Thanks But No Thanks, one of the other shortlisted songs, for the departing host Humberto Tan.

Late 2019, Waylon released his sixth album Human; early 2020, he announced that the fifth edition of his Ahoy concert-series will be devoted to Dutch(-language) pop classics.