Here are my two: One fast, fixed Fuji, meant for longer rides and getting to work and such; one slow, stylish Specialized, my coaster brake cargo machine for grocery store duty.
The Fuji is about 60 cm, probably from the 80s, was once a 12-speed, now goes 42-15 with 700x35s for the potholey Boston streets, slightly chopped moustache bars for multiple hand positions, and a MTB-style front brake for when I'm wearing dress shoes that don't fit snugly in the toe clips.
The Specialized is maybe 17", features a unique and durable electrical tape coating, 44x19 cruiserrific drivetrain, special two-part seatpost (BMX gooseneck inside a standard MTB post), and the mighty milk crate, which has been known to carry a week's worth of groceries. Also, a generator light and a bell.