I’ll never forget my first time on a Sportster. It was in Gulfport, Mississippi, the summer of ’89. A 6-foot 1-inch tall redhead named “Mama Cass” who I worked with at a beachfront restaurant facing the Gulf of Mexico asked me if I wanted to go to the All Harley Memorial Day Blowout with her. On her bike no less. Which is good because I didn’t have one at the time. My riding experience included learning to ride on my friend Paul’s 1984 Honda Ascot 500 and a few spins on a Rebel. I was stoked at the chance to mount her Sportster. To me, I was moving up into the big leagues.
I met Mama Cass at her house that afternoon so we could ride over to the Gulfport Dragway. She had an 883 that had been bored-out to a little over 900cc with a chopped-out front end and custom bars. She gave the root-beer-brown bike a few kicks in her garage but it only flooded out and filled the space with gas fumes. I opened the garage door to let the fumes out while she went in the house to freshen up.
After letting the bike sit a few minutes, I climbed on board, not really expecting it to fire up and gave it a kick. The knee-jerking kick starter sparked the V-Twin to life. The ensuing thunder vibrated through the thin slats of the garage, across the yard, through the walls of the house, and rattled the porcelain john Mama Cass was sitting on. She came running out of her house, still pulling her pants up, scared that I was stealing her bike. She was relieved to see I just wanted to see if I could start it up.
We rolled it out of the garage. She jumped on back while I steadied the bike. From the combination of a tight clutch, too much throttle and a rookie rider behind the handlebars, the torquey Sportster’s
front wheel popped up when I shifted into first, our heads snapped back and Mama Cass almost dumped off the back. She squeezed the breath out of me and let out a whoop. I held it straight and we came back down, so I shifted into second and headed off to my first biker blowout. Thus was born my first experiences on a Sportster.
I’m sure that in its 50 years of rolling off the Harley-Davidson assembly line, the Sportster has been responsible for numerous fond memories like mine. When you’re the longest c
