I started in 1996 with a Wheeler mountain bike - all that's left from back then is the frame.
In 2002 finally got my road bike - a 2001 model Argon 18 Helium. Very cool bikes from a Canadian bike company.
In 2005 I found a really great Honda VFR (2001 - pre-VTEC - silver, the fastest VFR colour!) and have been enjoying it since then...
And now, just last week, put a deposit on my newest in the collection - Cervelo's P2C (another great Canadian bike company!). Did a try-a-tri this summer and will be doing the half-ironman in Muskoka next September! The P2C Photo is from their website...