Marv

I would argue that the BMW 320i (the original 1970s & 1980s car) is or was closer to the 2002.

The 128i is simply too modern.

pdxmotorhead

I owned a 318ti for a long time, never understood why everybody wanted to swap them. up ,, its was fun daily, didn't have the power of my 996 ,,
But it was super on gas, was fast enough to never feel like your a cone in traffic and in twists totally entertaining, it loved to slide,
one of the most controllable cars I've owned.

Argeo

I think ya’ll missing the boat if you don’t mention a Boxster 986 Base. Porsche DNA and the handling/braking is hard to beat. Put that top down and your having fun. Like a Miata but not punishing long distance. Yeah not that quick in the zero to sixty thing but that’s only one factor unless your a drag racer.

Lady Silver

I owned a 2002ti I think it was called, and I loved it. Bought it new and owned it for about 7 years. But it never replaced the 911T I should have bought instead, in my mind. The only complaint I had on the 2002 was it spent too much time in the shop. Stuff would wear out and I think I rebuilt the entire cooling system. But it was comfortable on a trip, good storage, and great handling on the twisties. I was tempted on the 320's when they came out but went to a 528 instead, which was a very comfortable cruiser but definitely a sedan.

blacksquid

This is an interesting exercise. I've driven many of the cars mentioned so here's my take

1. 1999 996 C4 Cab - The most complete car I've had the pleasure to drive, especially after the FSI Stage 1+ rebuild
2. 2011 BMW 135i Cab - Just a fun car to drive
3. 2007 BMW Z4 M Coupe - I loved the aesthetics of the car but the stock suspension was pretty harsh and that CDV
was just horrible
4. 2013 Mercedes Benz C63 - Monster engine in a little bitty living space
5. Mazda R8 - Kinda cramped and the interior wasn't the best. Traded it sight unseen for a 2004 Prius.

theprf

I was very tempted, you could get then in the high 30's with "high mileage" in early 2020. Not so much any longer...
But they have problems too. Oil starvation in high G corners and oil pumps that shatter gears. Ford would replace engines no questions asked under warranty, my worry was when the warranty ran out.
So the dry sump endurance racing engine won out.

zbomb

It did for me too

As far as fun, or funner than a 996 for comparable money:

Miata with K Series
BRZ with LS or 2JZ
E36 with LS or 2JZ
C5 Z06
350Z with LS
240SX with a 2JZ
Focus RS

SoCal911t

I would argue that the e30 is also closer to the 2002 than the 128i

I decided when I retire that I'm going to thin the fleet by at least one car. I know it will blasphemy to some but I'm keeping the e30 and getting rid of the M5. The e30 is more fun to drive.

Porschetech3

Right .....I knew all this and had already previously discounted the new GT350 for those reasons , but when you brought it back up again I was taken back to the good ole days and "nostalgia" overwhelmed me for a bit, then I realized I would never trade my 996 for a GT350 of either vintage as a Daily Driver , although monetarily the 1966 version is not comparable..

mtnroads

My 5 window pickup is a rare '55 1st series Chevy 1/2 ton. I converted it to a 5sp from 3sp. It's a barnfind. It proudly sports a PCA decal.