* BlackSheepHit: The [[ClicheStorm cliché-heavy]] ballad "Then", in comparison to many of his songs being uptempos and/or novelties.
** In addition, his highest charting song on the Hot 100 is "Remind Me," a ballad with Music/CarrieUnderwood; Also different from his novelty songs.
* ChartDisplacement: "Whiskey Lullaby" is one of his biggest hits despite only getting to #3; this is because it was blocked by the one-two punch of "[[Music/KennyChesney I Go Back]]" and "[[Music/TimMcGraw Live Like You Were Dying]]".
* CreatorCouple: With actress Kimberly Williams-Paisley.
* MissingEpisode: "Without a Fight" was removed from the track listing of what would become ''Love and War'' due to the song bombing at radio.
* OneOfUs: "Online" and "Welcome to the Future" both make it known that he likes his video games and computing. The video for "Start a Band" also makes several completely accurate ''VideoGame/GuitarHero'' references.
* ProductionPosse: He usually tends to write with Kelley Lovelace, Chris [=DuBois=], and/or Lee Thomas Miller. He also uses members of his road band, the Drama Kings, on most of his albums.
* UnintentionalPeriodPiece:
** "Who Needs Pictures" is about the narrator finding an undeveloped roll of film before stating "Who needs pictures with a memory like mine". Nowadays, those pictures would probably be instantly accessible on a phone.
** A minor example. When "Online" came out, everyone had a Website/MySpace, so he mentioned it. He now changes the line to "Go check out my Website/{{Facebook}} page" when he sings it live.
* WhatCouldHaveBeen: Music/AlanJackson, Music/GeorgeStrait, and Music/GarthBrooks all expressed interest in recording "I'm Gonna Miss Her (The Fishin' Song)" before Brad ultimately cut it himself.
** Though, when Brad first started played it live (for a long time before it was officially released), he himself would preceed the song with a long banter saying that he'd pitched the song to Alan Jackson, who turned it down because he thought it was too goofy. As a result, Brad, who wrote it, kept it for himself.