In April 1995, four friends from the Denver, Colorado area, Reese Roper, Scott Kerr. Keith Hoerig and Micah Ortega began Five Iron Frenzy as a side project to another band. But the ska-core band quickly became their primary focus by August 1995, when Jeff Ortega (Micah's cousin), Dennis Culp, Brad Dunham and Andrew Verdecchio had all joined the band.

Unsigned and on their own, Five Iron Frenzy booked 60 shows within 8 months, and shared the stage with the likes of MxPx, Goldfinger, Mealticket, The Pietasters, Johnny Socko, MU330, Save Ferris, Less Than Jake, The Descendents, 10 Foot Pole, Mudsharks, and Buck-o-Nine. Halloween night that same year, Five Iron opened for Dime Store Prophets and Black Eyed Sceva of the 5 Minute Walk/SaraBellum Records label. Five Iron sent a buzz through the label and by August 1996, they were signed on SaraBellum Records. November saw the release of their debut Upbeats and Beatdowns.

Five Iron Frenzy's energetic Ska-core sound wouldn't seem to naturally lead to such sometimes intensely personal or political themes. But says Reese, "My lyrics are pretty personal. It's usually just real life that inspires me, something I see, or something I'm reading maybe."