* BreakthroughHit: "Family Bible" as a songwriter (a top 10 hit for Claude Gray in 1960); "Blue Eyes Crying in the Rain" as a singer.
* CreatorCouple: His second wife, Shirley Collie, was also a musician. She played bass for him for a while, and sang duet vocals on his first chart hit, "Willingly".
* FanNickname: The Red-Headed Stranger
* MoneyDearBoy: Thanks to a combination of his accountants from Price Waterhouse not paying his taxes for years and some bad investments in TheEighties, the IRS seized most of Nelson's assets in 1990, claiming he owed them $32 million. His attorney managed to negotiate a settlement down to $6 million, leading him to record ''The IRS Tapes: Who'll Buy My Memories?'' in 1992, a highly acclaimed double album performed by him alone on vocals and guitar, to pay off the debt.
* [[TheShelfOfMovieLanguishment The Shelf of Album Languishment]]: His gospel album ''The Troublemaker'' was recorded in 1973, rejected by his label, then released 3 years later by his new label.
* FormerTropeNamer: Ten With A Two, now BeerGoggles.
* VitriolicBestBuds: With Waylon Jennings. Willie is pretty easy-going, but Waylon was fairly HotBlooded, and they kept getting into disagreements that would leave them apart for a while, then reunite for more music. A perfect example of this can be found in the biography "Willie Nelson: An Epic Life", which details an incident from the "Highwaymen" tour, where Waylon got the idea in his head that Willie was actively angling for higher billing/more money. Fortunately, the crew of the show were able to get him past this by simply pointing out "Waylon, it's ''Willie''. You really think he gives a crap about that kind of thing?". Sadly, they were in the middle of one of these "breaks" when Jennings died of complications from diabetes.