* [[BreakawayPopHit Breakaway Country Hit]]: Both "Heartland" and "I Cross My Heart" off the ''Film/PureCountry'' soundtrack went to number 1. The movie? Not so much.
* FountainOfExpies: He was pretty much the go-to model for the "hat act" craze of the 90s.
* NamesTheSame: Somehow, he ended up recording two different songs both titled "She'll Leave You with a Smile" only five years apart. Only the latter was released as a single.
* OldShame: Averted, as he still performs many of his earlier hits in concert, including his debut single "Unwound." Likely the only exception was his second single, "Down and Out" (a No. 16 song in the fall of 1981), which George has stated was not one of his favorite songs and noted he would never consider releasing, much less recording, today. Indeed, the only places to find "Down and Out" are on his debut album, ''Strait Country'', and his first greatest hits album; it does not appear on any other of his greatest hits albums or his 1995 box set ''Strait Out of the Box''.
** He hated his first music video, for "You Look So Good in Love", so much that he asked that it be withdrawn from rotation. He has very rarely done a music video since, and the few he's done since are largely {{Performance Video}}s.
** Strait also has since said his hit "You Know Me Better Than That" is not a song he would record today; alas, he hasn't played it live since it was an active single.
* ProductionPosse: He has had nearly the same batch of session musicians and the same producer (Tony Brown) on every album since ''Pure Country'' in 1992. In addition, nearly every album dating back to his first has had at least one song written by Dean Dillon.
* WhatCouldHaveBeen: He had both "Everybody Wants to Go to Heaven" and "Love Done Gone" on hold, but they ended up being recorded instead by Music/KennyChesney and Billy Currington, respectively.