"When I Get On A Roll" is a song by Jacob Bryant about his tendency to go overboard when he gets caught up in the moment. The song talks about how he can outdrink any man, and woo any woman in the world when he gets on a roll. He admits that he isn't proud of his behavior, but he can't help but feel invincible when he's under the influence of alcohol. The lyrics also mention that when he's on a roll, he feels like he's flying on whiskey wings and can't be stopped. He recognizes that his behavior could be a phase or a couple of days of heartache, but he can't control himself when he gets on a roll. At the end of the song, he asks for forgiveness from Jesus for his past behavior and promises that he won't do it again, but he acknowledges that he can't guarantee that he won't get on a roll again in the future. Overall, the song is a cautionary tale about the dangers of excess and the consequences that come with losing control.