Will the First generation Prius ever be considered a classic car?

Never. Some things are best forgotten

A classic piece of ****.

No.

Probably, but not like a vintage Maserati, so don't think you can retire on it

Probably not. I am still driving my 2002, but it lacks collector appeal.

On the plus side, it is an example of the beginning of the Prius dynasty, which will be on record as the dawn of popular hybrid vehicles. It is fairly fuel efficient and is perfectly adequate transportation. It is not as plentiful as the original VW beetle, which is now a classic. It also has some recognizable unique features, like the driver's side C-pillar battery vent and the odd gear selector.

On the minus side it is not the Greatest Generation. It is remarkably reliable by contemporary standards - mine needed its first actual repair last year: the inverter coolant pump died. However, by the standards of later Prius models it doesn't make the grade. First gen problems included Triangle Of Death when the weather turned cool each fall if the throttle body is not cleaned annually or poor quality gasoline is used. The steering rack can oscillate in reverse, and for the 2000 (JDM) the throttle position sensors could fail, causing the system to go to idle.

I expect to have mine long enough to find out. It is 16 years old now and going strong. At 25 years I will know.

A car is classified as a Classic when it's 50 years old.

When pigs learn how to fly.

right next to a YUGO

Over my dead body!