From simple to sexy, this great bicycle is my best, and it has seen many upgrades. I purchased it in 2006 for $20 in clean original shape. I swapped the handlebars out in favor of some Northroads from a Raleigh 3 speed, and I put on a friction shifter to work the rear derailer. I removed the front derailer. I changed the tires to some cheap IRC slicks, and rode the bicycle just like that for a long time.
The 1997 Diamondback Outlook, later known as 'Tall Cool,' was the bicycle that I parked outside in Philadelphia so I wouldn't need to take my 'better' bicycle up and down a set of stairs just to run a short errand. Tall Cool stayed parked on the corner of 46th and Locust for many months.
I added a rack and used hose clamps to securely attach a milk crate. After that, Tall Cool seemed to have a foot in the door, and became my main bicycle in that sneaky manner. At one point, I chose TC for a long summer trip to the beach. We went 120 miles in a day just with the milk crate setup and bulky tires. The inverted tread of the tires hummed across smooth pavement, and the cheap stock saddle did not feel good at the end of the ride. But TC proved itself to me that day.
Major upgrades in components came after recovering this bicycle months after it was stolen. Someone took off on the bike when I left it leaning on a wall for a minute to change clothes in my van in Key West. I used my status as bicycle shop employee to order new parts for what I thought would be a replacement bicycle. I bought a similar Diamondback frame on eBay, and equipped it with many nice parts. Soon after completing that build, I saw my beloved 1997 Outlook parked outside a grocery store unlocked. I hopped on and stole it right back!
I was overjoyed at recovering my bicycle. I took it right to the shop where I worked, and soon replaced all the parts with newer "better" components.
The next summer I went on a bicycle tour from Philadelphia to Bangor, Maine. Then I took a bus to Montreal and continued to ride along the Petite Train Du Norde, a beautiful rail-trail conversion that took three days to traverse. The trip took me one beautiful month to complete. I met wonderful people and camped wherever I found some trees at night.
Back in Philadelphia one drunk night, I crashed Tall Cool into a tall curb and bent the fork back considerably. I took a ride home in a friend's car and TC sat unused for quite some time. Back in Key West for another season, I met friends and had a need to ride the bicycle again. I had my father drop it off at a bicycle shop to be shipped down. Upon arrival, I rediscovered just how bent the fork really was. Ouch.
I went to Tightwad Bicycles off Duval St. and spied a black Diamond Back Outlook of the same exact dimensions. The bicycle was tucked amongst dusty-sexy mannequin legs and many doobies from marijuana cigarettes. The fork was a nicer Tange model with tapered fork blades. The bicycle was most likely the 1995 Diamond Back Outlook model. I paid $120 and took the new Outlook to where I was staying. I swapped the black fork onto Tall Cool, and everything in life was perfect again.