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I'd pull off the CLK GTR and put the 300SEL 6.3 on there instead. And the SL65 is nice and all, but something iconic has to be said about a roadster that spans 2 decades of production (R107).
As for the 190E 2.5 16 Evolution II, it seems to me it'd be more likely to grab a spot on the list for appearances in the GT series than actual "Street cred"... I'd say The Hammer would deserve that spot.
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Back in the saddle - 1972 280SE 4.5
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