Did Obito just beat Itachi's record?
Of pwning himself? Lol
Despite all the powers that was bestowed upon him, he still ended up pwning himself (by Nardo's TNJ) due to his sissy nature, which can be traced back to his fanboyism of his crush on a fodder called Rin.
Unlike Sasuke vs Itachi battle, at least Sasuke had a major hand in hastening the end of Itachi's life by forcing him to use Susanoo,
and by no means free like the TNJ spell cast on Nagato and Obito.
Itachi didn't just stand there and let asked Sasuke to kill him (granted that he wasn't fully trying), that's the major difference.
It's no wonder why Madara replaced him, just as I predicted Lol
Others worthy contestants include Haku, Sasori, Nagato who did similar things.