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I think most of the cars mentioned can be found used, "certified pre-owned" if you want, or just buy them from the original owner - overall IMHO a better deal than buying a new S4. I don't think the S4 has changed all that radically in the last few years.
One thing I will say is that some of these Audi's are a bear to work on, for example having to take the front end tin all off to do a timing belt/water pump service. That and some of the front end suspensions are known to not last very long and again a bear to work on/expensive parts.
For less than half the OP's budget he can get one of the very best "real" M3's around, for a fun car it's hard to beat if you don't want to spend for an F-car. Well cared for, it won't lose any value, and may go up.
I think most of the cars mentioned can be found used, "certified pre-owned" if you want, or just buy them from the original owner - overall IMHO a better deal than buying a new S4. I don't think the S4 has changed all that radically in the last few years.
A major recent change is a shift from the 4.2L V8 to the 3.0L blown V6. This apparently has improved driving dynamics by improving the weight distribution -- less weight over the snout and in particular less weight in front of the front axle.
Hey guys thank you all for the helpful replies. I'm kinda leaning toward a cpo m5 or Audi s8 if I can find one. My question though are those cars still fun considering how heavy they are? And to better help you out the most I'm willing to spend is 75k.
Well those cars are definitely in a different league than the S4. As for whether they can be fun, a lot of people find them so. Depends on what sort of driving dynamics you expect from a sports car. You won't mistake an M5 for a Lamborghini Gallardo, but you won't mistake it for a Lincoln Town Car either. The best way to answer the question for yourself is test-driving.
Would also consider leasing a new Merc C63; test-drive any car on some interesting rds (both fast urban fwys and challenging twisties (if any nearby)...and bumpy urban roads) to really judge....lots of famous, costly cars may be fun on a dry, smooth track in Podunk but are worthless in real world
Very enjoyable exhaust note upon start-up and at any speed; strong NA tq (more tq at lower RPM than Ferrari's NA V12 599); Merc safety; anecdotally excellent reliability; daily-useability for urban commuting and wkend fun; stealth factor of a sedate-looking small MB both at office and vs cops....hand back car at end of 2-3 yr lease for another new AMG...only real maintenance costs are tires and oil changes
My sense from AMG addicts in snow regions is that proper winter tires make AMGs fully capable for daily winter use in NYC or Chicago vs any AWD (which also needs winter, not all-season, tires for decent braking/handling in cold or snow)
If he could find a good USED R8 for, say, $60K I'd recommend that!
lol You should go up to Roger Beasley in Austin and offer them that on a nice used one.
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on a nice used one. 
