Spider-Man and Wolverine are two of Marvel's biggest icons. The web-slinger and the X-Man have shared many adventures over the years, filled with triumph and tragedy. One time-spanning saga, however, brought Spider-Man and Wolverine closer than ever before.

In their earliest team-ups, Spider-Man and Wolverine were reluctant allies at best. Peter abhorred Logan's violent, murderous ways and Logan couldn't stand Peter's constant quips and naiveté. Of course, the wall-crawler and Canucklehead were members of the New Avengers, where they managed to work as a semi-functional team.

Yet during individual team-ups, it was very clear that Peter and Logan could only handle so much of each other.  It wasn't until Astonishing Spider-Man & Wolverine, by Jason Aaron and Adam Kubert, that Marvel's biggest heroes developed a real bond.

Related: Wolverine: A Weapon X Ally Is Back With a BRUTAL New Job

Spider-Man Wolverine Brothers

This mini-series began when both Spider-Man and Wolverine happened upon a bank robbery. The lesser-known villain The Orb was in charge of this operation, stealing a bag of rare jewels. These glowing-green artifacts transported Spider-Man and Wolverine back in time to the Cretaceous Era. Once there, the two heroes went their separate ways. Peter devoted himself to science, attempting to find a way back home, while Logan mentored a clan of cavemen called the "Smallfolk."

Suddenly, a meteorite with the same glowing jewels hit the Earth, flinging Spider-Man and Wolverine into the far future. Again, both Avengers took vastly different paths. Peter became a teacher to the future Smallfolk, while Logan spent his time fighting robots in a training simulation. Although the future Smallfolk worshipped him as a messiah, Wolverine refused to accept this role. When Doctor Doom, who had taken over Ego, The Living Planet, arrived, Spider-Man brought out the powerful Phoenix Gun to stop him. Wolverine, however, wouldn't let Peter sacrifice himself, firing the Phoenix Gun instead of the web-head.

Guilty over Logan's death, Peter brought him back with the Cosmic Cube. Wolverine was angry, however, since he was just about to see his long-deceased mother. Once Logan returned, he and Peter got into an intense physical fight. Immediately afterwards, Spider-Man and Wolverine were transported back in time again, although in separate areas. Peter witnessed Logan's youth, where he was hunted by his brother, Dog. Meanwhile, Logan saw Peter's time as a professional wrestler, right before he learned about responsibility. This moment gave each hero a deeper understanding and sympathy for the other's plight.

Spider-Man and Wolverine were then reunited in the Mojoverse, where it was revealed that Mojo orchestrated this entire time-spanning adventure as a reality show. Even the girl who Peter had been dreaming about, named Sara, was cast by Mojo as a love interest. Spider-Man and Wolverine defeated Mojo and his henchmen before Wolverine was taken over by the Dark Phoenix.

Related: Spider-Man: How House of M Gave Peter Parker His Dream Life

Fortunately, Spider-Man talked Wolverine down, and the heroes, along with Sara, were transported to the 18th century. Peter and Logan spent three years in this era, gradually becoming brothers. Peter had also developed a romantic relationship with Sara, to whom he was going to propose. Yet the ring that Peter made was from the glowing green jewel, incidentally sending Spider-Man and Wolverine back to the present. Although Peter found Sara in the present day, she had no memory of him. Heartbroken, Spider-Man left Wolverine without a word.

Now, Spider-Man and Wolverine are in completely different worlds. Peter remains in New York City, but Logan lives on the mutant nation of Krakoa. Neither one of these heroes is an Avenger anymore, and mutants haven't typically been interacting with other heroes as much as they used to. Of course, Spider-Man and Wolverine did team-up with Franklin and Valeria Richards during "Empyre," reforming the "New Fantastic Four." This adventure, just like Astonishing Spider-Man & Wolverine, demonstrated that the two heroes should team up more often.

For one thing, Peter and Logan make a perfect "buddy-cop" duo. Peter is the comic relief and brains, while Logan is the no-nonsense muscle. Yet their rapport goes much deeper than this. Spider-Man has shown that he is a genuinely good person who Wolverine can trust, outside of the X-Men, which is pretty rare. At the same time, Logan always has Peter's back, much like an older brother.

Astonishing saw Spider-Man and Wolverine learn more about each other, develop a brotherly dynamic and even make some major sacrifices for each other. In the future, the bond that they formed in Astonishing could inform Spider-Man and Wolverine's team-up dynamic. Overall, Astonishing Spider-Man & Wolverine illustrated a strong rapport between Marvel's biggest icons.

KEEP READING: Spider-Man: How Secret Wars Gave Peter Parker the Symbiote Costume