The Mad Caddies sound has influences from broad ranging genres including ska (especially ska 3rd wave), punk rock, hardcore punk, reggae, dixieland jazz, Latin music, polka, cowpunk ("Crew Cut Chuck"), and sea shanties ("Weird Beard").

[1][2][3][4] Founding members Chuck Robertson, Sascha Lazor, Todd Rosenberg, and Carter Benson started the group while attending Santa Ynez Valley Union High School.

[1] In the band's early beginnings in the mid-1990s, they performed as Cracked Macaroni at Santa Ynez Valley Union High School.

In 2023, the band signed with SBÄM Records, announcing their eighth studio album, Arrows Room 117.

In 1999 Robertson, Sascha Lazor, and Benson started a side project with Derrick Plourde called Sweet Action.