Thanks to "Head Over Boots" and "Dirt on My Boots" -- a second single that bested its predecessor, reaching number one on Country Airplay and crossing over into the pop Top 40 -- California Sunrise turned Jon into a star. The album stayed on the charts through 2018, spinning off additional hits: "Heartache on the Dance Floor" went to three in 2017, "She Ain't in It" peaked at 21 that same year, and "Night Shift" reached 14 in 2018.

Jon released his third album, Heartache Medication, in September 2019, which spawned the hits "Ain't Always the Cowboy" and the chart-topping title cut. The following year saw him release Rancho Fiesta Sessions, an eight-song collection of cover songs.