It's hard to imagine a time when Marvel movies weren't regularly breaking box office records and spawning multi-film franchises, but until the property coalesced into today's MCU, these adaptations had a decidedly checkered history. Believe or not, these earlier attempts date back to 1944, with the Captain America serials produced by the ancient Republic Pictures. Many see Jon Favreau's 2008 film Iron Man as the breakthrough that forever changed Hollywood's now torrid love affair with comic book movies, but adapting these superhero franchises had plenty of fits and starts.

Some of these earlier attempts, such as the Sam Raimi Spider-Man trilogy began breaking down the wall by the early 2000s, netting huge box office returns while still maintaining some of the quirkiness of Marvel adaptations from the 80s and 90s. Here's a look at some of those earlier forays and why we are still nostalgic for them.

Related: Everything We Know About Sam Raimi’s The Last of Us (& Why It Didn’t Happen)

10 The Punisher (2004)

While there's never been a more perfect actor to portray Frank Castle than Jon Bernthal, Thomas Jane did an admirable job of tackling the role of moribund ex-FBI agent turned vengeful superhero in The Punisher. This installment was a huge upgrade from the Dolph Lundgren version, while still maintaining some of the silliness of the 80s and 90s Marvel films. The movie actually had a pretty tremendous cast, with John Travolta showing his range as the villainous Howard Saint, and a young Ben Foster giving a great performance as the heavily-pierced Spacker Dave.

The film didn't quite hit the nail on the head when it came to capturing the darkness of the comic book, as the main characters battled on the mean streets of...Tampa Bay? Still, we got some great action sequences throughout. The Punisher was certainly worth the price of admission, giving the audience chills when Roy Scheider appears as Castle's father, rifle in hand, giving us all the Jaws flashbacks we never knew we needed.

9 X-Men: The Last Stand

By the 2006 release of X-Men: The Last Stand, 20th Century Fox had begun to understand that over-funding Marvel scripts was the only way to generate the star power and visual effects necessary to net the box office gains that these franchises were capable of. Thusly this movie had the biggest budget of any Marvel film to date at $210 million.

It easily doubled that number in worldwide box office gross, and expanded the number of characters that could be jam-packed into a single Marvel movie, a blueprint that is now oft-used for movies like Avengers: Endgame. Even though the MCU had yet to come to full fruition, this was one of the films that helped solidify that iron-clad, bankable brand. The movie was pretty exciting too, with some interesting casting choices like Kelsey Grammer as Beast and Vinnie Jones as Juggernaut.

8 Spider-Man

The Spider-Man franchise wasn't always the sure bet it has become today. There were a few futile attempts to adapt the character to the screen, those being a 70s tv series and a Japanese manga film that tried to incorporate the superhero. So when director Sam Raimi took the reins of Spider-Man, which had languished in development hell for nearly three decades, studio executives were quaking in their boots until the films $100 million opening weekend laid those concerns to rest.

The greatest thing that Spider-Man introduced to the superhero genre was a centralized love story, and a plot that focused as much on quality acting performances and dialogue as it did on set pieces. Tobey Maguire still presides as the most perfect fit for Peter Parker, and the movie will be remembered as much for its famous upside-down kiss as any of the web-shooting action. Raimi clearly understood the importance of tone, and his combination of silliness with visually compelling action proved that you didn't need a barrel-chested, one-liner-spouting superhero to bank big on a comic book franchise.

7 Blade: Trinity

It's funny to think that there was a time when Ryan Reynolds would take second billing to Wesley Snipes in a movie, but back in 2004 Reynolds was still working his way up the ladder, and Snipes was at the peak of his powers with the Blade franchise in full swing. Blade: Trinity is one of the better Marvel movies from the early 2000s, ironically featuring an array of indie-darling actors like Parker Posey, Patton Oswalt and John Michael Higgins. Even theater legend Eric Bogosian makes an appearance.

At the core of the movie, however, is the success of the odd couple pairing of Snipes and Reynolds, and it was a pivotal role that vaulted Reynolds into action star territory. It is hard to imagine he would have otherwise been considered for Deadpool over a decade later had he not been so perfect in this role.

6 Ghost Rider

There was a time, back in the early aughts, when Nicolas Cage was less of a full-on parody of himself and more of the believable action star that we saw in Ghost Rider. If the measure of an actor is his commitment to a role, then Cage's performance as Johnny Blaze measured off the charts. The many critics who panned this movie completely missed the point, which was its pure entertainment value.

From the sonorous narration and acting of Sam Elliott to the exceptional visual effects, the audience got a rip rollicking ride on the back of Johnny Blaze's motorcycle. Add to that some hilariously unexpected performances from the likes of Peter Fonda and then-unknown Rebel Wilson, and Ghost Rider provided an experience fairly unique to the rest of the Marvel adaptations. Still, it maintained much of the pre-MCU silliness that allowed us to not take it too seriously.

5 X-Men

In the scope of the earlier Marvel movies, X-Men may have been just as crucial to the elevation of the big-budget comic book adaptation as Spider-Man and Iron Man later were. The movie made nearly $300 million against a $75 million budget, and proved you could include a vast array of X-Men characters without distracting the audience or deviating from its central plot.

It also had a darker tone than many previous superhero movies, with a cold open set in Nazi-occupied Poland to introduce Magneto's origin story, and a more realistic representation of what a mutant world would look like cast against our own. Wolverine's relationship with Rogue also humanized these characters in a way that made audiences more invested in their story arcs, and laid the groundwork for the development of other films based around individual X-Men characters.

4 Fantastic Four

The 2004 adaptation of Fantastic Four was another large stepping-stone in the development of the MCU. Only a decade earlier, B-movie pioneer Roger Corman had attempted to adapt the comic into a live-action movie, with decidedly poor results.

The newer version proved to be a box office boon, and showed how much a large visual effects budget could improve this franchise. Despite its 28% approval rating on Rotten Tomatoes, this is actually a really fun movie, with some of the best set pieces from any of the early 2000s Marvel films.

3 Blade

Originally a supporting character in Marvel comics from the '70s, Blade was the perfect character for an actor of Wesley Snipes' physicality. It also proved to be a much more successful adaptation of a dark comic than Spawn had been only a year earlier. Marvel adaptations up to this time had veered away from graphic violence and gore, but Blade embraced it — much to the delight of audiences that reveled in waching Snipes' daywalker navigate through incredibly choreographed fight sequences.

It is also a pioneering film in its representation of an African-American star in a leading action role at a time when Hollywood was still lagging in that respect. Add to that some fun performances from Kris Kristofferson, Traci Lords and Donal Logue, and Blade remains one of our favorite Marvel movies to date.

Related: Blade Reboot Will be Much Darker Than Anything Else in the MCU

2 Howard the Duck

Known to this day as one of the biggest flops in movie history, Howard the Duck has aged like a fine wine. It's pretty funny to think that George Lucas was developing this at the same time he was making his Indiana Jones films, given the incredibly zany script and completely of-their-time 80s characters. Still, it contains all the earmarks of a great cult movie, from the outlandish costumes to the suprisingly innovative visual effects developed by Lucas' Industrial Light and Magic.

The film introduced audiences to Tim Robbins, and no proper 80s movie would be complete without Lea Thompson and the uber-creepy Jeffrey Jones. In fact, it's suprising that the MCU hasn't made an attempt to reboot this franchise to date, other than Howard's brief cameos in the Guardians of the Galaxy movies.

1 Spider-Man 3

Other than The Avengers, there is no more bankable franchise in Marvel's portfolio than Spider-Man, which reached its peak with Spider-Man 3. Still, since the advent of the MCU the franchise has never quite reached the heights of pure entertainment found in the third installment of Sam Raimi's trilogy.

It was a high watermark for acting performances in the franchise, marking some of Kirsten Dunst's best work, and still makes us long for Tobey Maguire's humanistic quality as Peter Parker.