Most of my earlier experience with Cannondale's was from working in a bike shop in London at the beginning of the new Millenium. Evans Cycles, The Cut to be precise. When they weren't getting stolen off the shop floor and sold on Sundays at Brick Lane market, then were coming back - cracked where the shop moniker for these became 'Crack and Fail'.
Around this same time the Bad Boy was carving a chunk into the commuter market as a sleek machine for getting around. A few bike couriers I worked with had them and they were a light and well thought out bike for Central London with the HEADSHOK and disc brakes. Not dissimilar to my first courier bike - a Trek 8000 MTB with slicks which I'll add also cracked and failed after 6 months on the street.
Then there was this classic from the late 1998/99 with the famed Hutchison Pythons that every cool kid from VICMtb had on their hoops - Cadel Evan's Cannondale CAAD 4 which now resides at the National Museum of Australia.
This 'retro' Cannondale R1000Si road bike fell into my lap in a very sorry state, destined for hard rubbish. Like any good car restoration, if you throw enough time, labour and coin at it you'll always come away with something respectable.
It had a near complete Campagnolo 9s Chorus ensemble down to the hubs, laced to classic Mavic Open Pros, Deda cockpit. The brakes, chainrings, and drivetrain were shot - so they all got replaced. The Chorus alloy levers refused to shift, and unable to find a suitable spare, Xenon levers were easily sourced and suited the black stealth vibe of this machine.
Ready for another 10,000km or more!