If you really want to go big, might I suggest the very first MDS with Drew, where Adam won a million dollars by being within $1,000 of the ARP of his Showcase (although this would later be lowered to $500). Also Michael scoring another million-dollar DSW and Cynthia winning the big prize in Clock Game in the same series are must-see as well. Honorable mention goes to the 25th and 30th Anniversary Specials, plus the one Special in 1986 where Velma mauled Bob after winning $11,000 on the Big Wheel. Then again, any primetime special where the host wears a tuxedo is worth watching, because IMO, that's the way it should be done! (which may be the reason why I was somewhat disappointed that Bob was in his regular daytime attire when he hosted the MDS from 2003-07)
If we were to restrict this to the daytime edition, then any episode from the Bob/Rod era will do, as that was the golden age of the show. Also recommended is the transition period that would allow us to see how much had changed from Bob's final season to Drew's first.
