Black Sheep Hit: "Red Solo Cup" is his most popular crossover hit. It's an acoustic novelty song, and one of the very few singles of his career that he did not write.
Career Resurrection: He managed to have two. The first came after he moved from Mercury to DreamWorks, when his second single for the latter label ("How Do You Like Me Now?!") became the biggest country hit of 2000 and led to a hot streak that carried him well into the first half of the decade. He cooled off considerably upon moving to Show Dog, but had a minor resurgence in late 2011-early 2012 with the viral hit "Red Solo Cup".
Near the end of his tenure with Mercury, he was working on a new album, but label execs didn't like it. They chose only two songs off the would-be album, "Getcha Some" and "If a Man Answers", released both as singles off a Greatest Hits Album, and asked him to try again. When they didn't like the next two songs that he sent, either, Toby demanded out of his contract and took said songs to DreamWorks records. That label launched him with "When Love Fades", but when it bombed, he asked that it be pulled and replaced with a song that Mercury had rejected titled "How Do You Like Me Now?!" — a good move on his part, as that song was a six-week #1 smash, his first Top 40 pop hit, and the biggest country hit of 2000.
A self-inflicted example since the move to Show Dog. He always pulls singles at the 15-week mark, regardless of how high they are on the charts, just to ensure he always puts out one album a year. This pretty much torpedoed his Bullets in the Gun album.
Name's the Same: Comedian Tim Wilson also recorded a song called "High Maintenance Woman" (which he co-wrote with Danny Simpson), in which the title woman falls in love with a maintenance man. Keith wrote his own "High Maintenance Woman" by himself and did not notice the similarities at first, but being friends with Tim Wilson, he gave Wilson and Simpson co-writers' credit on his song.