Willie Nelson & Annie D’Angelo — 29 Years

Having received critical appreciation for his albums called Shotgun (1973), Red Headed Stranger (1975), and Stardust (1978), it is pretty safe to say that Willie Nelson was one of the most popular singers/musicians of that era. His album called Ride Me Back Home (2019) has earned him a Grammy Award for the Best Solo Country Performance.

Willie has been married four times so far. Although his first three marriages didn’t work out, his fourth one has broken all the barriers that the first three might have set. Willie and Annie D’Angelo have been together for about 29 years now.