* BlackSheepHit: "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.
* CareerResurrection: 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".
* ChartDisplacement: A lot of his #1 hits have long been forgotten, but averted overall as "How Do You Like Me Now?!" and "Beer for My Horses" are among his most iconic songs. Meanwhile, "Red Solo Cup" zig-zags this as it only got to #9 on the country charts but is his biggest Hot 100 entry at #15.
* CreatorBacklash: He has reportedly expressed dislike for his cover of Music/{{Sting}}'s "I'm So Happy I Can't Stop Crying".
* DevelopmentHell: His 2015 album ''35 MPH Town'' was delayed at least twice due to underperformance of its singles ("Drunk Americans" and the title track), and the followup has also stalled out due to "A Few More Cowboys" barely denting the charts.
* ExecutiveMeddling:
** 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 GreatestHitsAlbum, 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 Creator/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 was usually pulling 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. The revolving door finally stopped with ''Drinks After Work'', which he gave some more breathing room on either side.
* HeAlsoDid: While very rare, Toby has had a couple outside cuts: "Slave to the Habit" by Shane Minor and "Starkissed" by Music/CledusTJudd. He also co-produced some albums by other acts on the Show Dog roster.
* NamesTheSame: Comedian Creator/TimWilson 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.
* OldShame: In an interview with ''Billboard'', he said that he was never a fan of his 1995 hit "Upstairs Downtown" because he didn't think it had much hit potential, and that he would have rather had "Boomtown" as a single. It's also been said that he regrets covering Music/{{Sting}}'s "I'm So Happy I Can't Stop Crying" as a duet with Sting.
* UnintentionalPeriodPiece: "Courtesy of the Red, White and Blue (The Angry American)" is so very, ''very'' obviously tied to the era immediately after 9/11.
* WhatCouldHaveBeen: "I Wanna Talk About Me" was originally planned to be Music/BlakeShelton's debut single, but his label rejected it as too risky for a new artist.
** "Clancy's Tavern" was originally going to be the second single from that album, but stations started playing "Red Solo Cup" instead.