Ones who bested death the most in the manga

[Nick01]

Obito, Madara, Naruto, and Oro.

 

[NarutoX28]

Looks like you forgot Killer Bee, even with his limited screentime he....

Cheated Sasuke & Taka, cheated death via madara extraction and cheated death with Momoshiki.

It makes me wonder how Kishimoto would expect us to forget about surviving after a Bijuu extraction. Even Kushina couldn't survive for an extended period of time despite her high lifeforce.

 

[Chaosmark101]

Obito by far

 

[Kirin The Dragon Sage]

team jiraiya is soo sad.

 

[HiddenSound]

Orochimaru...
Victim of 3 different soul-sealing Jutsus (RDS, his own Fushi Tensei, Totsuka)
Got cut in half
Got punched in the head by Tsunade
Got slashed in the face by Kyuubi Naruto, whose claws seemingly punctured his skull
Got his throat torn to shreds by Kabuto
Got stabbed in the torso by Totsuka and laughed

And then there's the fact that he literally cut up Death itself, then survived when he was supposed to die there too

 

[-Haku Yuki-]

Obito he survived
getting crushed by rocks
getting stabbed by kakashi
tailed beast extraction
rinnetensei
and death itself for 5 minutes (with kakashi)