Mmm, that most likely would have been Nigel Short and his challenge for the title against Garry Kasparov back in '93. When asked by the media who he thought his challenger would be that year, Garry is famously quoted as saying "It'll be Short and it'll be Short".

Truth be told the games were tough slugfests, even though Kasparov won pretty handily in the end. Garry officially retired from competitive chess last year, ironically losing his final game to...none other than Veselin Topalov! But he will be remembered as one of the greatest, definitely. [img]smile.gif[/img]
However, the chess world hasn't quite been the same since the Kasparov vs Short match, since it was when the infamous split from FIDE occurred, resulting in the current bizarre situation of having two world champions, thus arguments reigning world-wide as to who it really is. Whilst Vladimir Kramnik is the classical champion in the long line of champions since Steinitz, having defeated Kasparov in 2000, Topalov is FIDE champion, an impressive winner of their large round robin world championship.
Hence, we have the idea of 'reunification' for the present match! (Although the story really is much more complex than this...)
As for Deep Blue and Deeper Blue, that's quite a controversial matter. Both have been retired by IBM after both defeating Kasparov back in 96 and 97. There's a quick report about it at wiki here:
http://en.wikipedia.org/wiki/Deep_Blue
Man Vs Machine matches are happening, usually with a humbling defeat for humanity. However, Kramnik obtained a 4-4 draw with Deep Fritz back in 2002, so perhaps not all hope is lost!
Game Four of the current match was a hard fought positional grind of 54 moves in which Topalov had a massive space advantage in which he sacrificed a pawn. 3-1 is the score to Vladimir's advantage. The tension can only increase as Topalov needs to find a win very soon!
Cheers,
CD