THEN AND NOW: Actors who played villains in the Marvel Cinematic Universe

He worked with Howard Stark, Tony Stark's (Robert Downey Jr.) father, and was the CEO of Stark Industries until Tony took over the position. Obadiah became Iron Monger after donning a suit of armor.

At the end of the movie, the character died from electrocution.

Two years after starring in "Iron Man," Bridges won his first Academy Award for his starring role in "Crazy Heart." He later earned two more Oscar nominations for his parts in "True Grit" (which starred breakout actress Hailee Steinfeld) and "Hell or High Water."

Bridges also reprised his "TRON" role as Kevin Flynn for 2010's "TRON: Legacy," which starred Olivia Wilde.

He portrayed the titular character in the 2014 film adaptation of Lois Lowry's "The Giver," appeared in the 2017 "Kingsman" sequel, and starred in 2018's "Bad Times at the El Royale" with Marvel's Chris Hemsworth.

Although Bruce Banner/the Hulk was portrayed by Edward Norton, the movie was technically part of phase one of the MCU. Norton later said that he parted ways with Marvel over creatives differences, which resulted in Mark Ruffalo taking over the role.

In "The Incredible Hulk," the titular character fought the Abomination as he wreaked havoc in New York. Rather than kill the Abomination, he had the villain arrested.

Downey Jr. also made an appearance at the end of the film as Tony Stark, mentioning a plan to form a team (which would come to be known as the Avengers).

The drama series lasted for three seasons between 2009 and 2011.

Roth also starred in Quentin Tarantino's 2015 movie "The Hateful Eight" and played Gary "Hutch" Hutchens on "Twin Peaks."

Tony Stark referred to him as his "least favorite person on Earth" and the two had a rivalry since Justin Hammer was the CEO of Hammer Industries and wanted to compete with Tony's tech.

Rockwell went on to earn an Academy Award nomination for his portrayal of George W. Bush in "Vice" with Christian Bale.

He's also starred in movies like "Seven Psychopaths," "Poltergeist," and "Jojo Rabbit." In addition, Rockwell starred on FX's "Fosse/Verdon" with Michelle Williams. He played real-life actor, dancer, and choreographer Bob Fosse on the show and nabbed an Emmy nomination for the role.

Vanko had his own qualms with Tony because his late father, Anton Vanko, was Howard Stark's disgraced former partner at Stark Industries.

He appeared in the star-studded 2010 movie "The Expendables" and portrayed King Hyperion in "Immortals" the following year.

Rourke also starred in "Frank Miller's Sin City: A Dame to Kill For" with Jessica Alba, Joseph Gordon-Levitt, and Josh Brolin.

Laufey was the biological father of Loki (Tom Hiddleston), Thor's adopted brother. Loki allowed the frost giants to storm Asgard and get a power casket at the start of the movie in exchange for them going back to their planet.

Loki also functioned as a villain in the movie and sent the Destroyer (an automaton) after Thor — but more on him later.

The show is based on comic-books written by My Chemical Romance front-man-turned-writer Gerard Way and illustrated by Gabriel Bá. Season two hit the streaming service in July 2020.

Since "Thor," Feore has appeared in "The Amazing Spider-Man 2" and guest-starred on Fox's "Gotham." He also starred on shows like "Sensitive Skin" and "House of Cards."

He became known as Red Skull after taking the super-soldier serum. During his fight with Steve Rogers/Captain America (Chris Evans) near the end of the film, Red Skull disappeared after touching the Tesseract. He was sent to the cosmos, but it was unclear where the villain ended up.

He played the character in 2012's "The Hobbit: An Unexpected Journey" and 2014's "The Hobbit: The Battle of the Five Armies." Coincidentally, those movies also starred Martin Freeman, who joined the MCU as Everett K. Ross in "Captain America: Civil War."

Weaving also starred in "Hacksaw Ridge" with Andrew Garfield (one of several actors who has portrayed Spider-Man on the big screen) and appeared on Showtime's miniseries called "Patrick Melrose," which starred Marvel's Benedict Cumberbatch as the titular character.

Red Skull had a notable return to the MCU in "Avengers: Infinity War," followed by 2019's "Avengers: Endgame." The character was revealed to be the Stonekeeper on Vormir, but Weaving didn't play the part. Instead, the role was portrayed by "The Walking Dead" star Ross Marquand.

Weaving told Time Out that he "loved" playing Red Skull, but said that Marvel offered him less money than he was originally told, and it was "impossible" to negotiate.

Early in the movie, the God of Mischief declared that he was "burdened with glorious purpose."

He went on to mind-control Clint Barton/Hawkeye (Jeremy Renner) and Dr. Erik Selvig (Stellan Skarsgard) using his scepter. Loki also killed S.H.I.E.D. agent Phil Coulson (Clark Gregg) by stabbing him in the back using the scepter, but he was brought back to life for his own ABC show, titled "Agents of S.H.I.E.L.D."

The Avengers defeated Loki and he was sent to Asgard to be a prisoner, but that wouldn't be the last fans would see of him. At the end of the movie, it was revealed that Loki was working for Thanos.

Since "The Avengers," Hiddleston has returned as Loki for "Thor: The Dark World," "Thor: Ragnarok," "Avengers: Infinity War," and "Avengers: Endgame."

At the start of "Endgame," Loki was killed by Thanos in front of Thor (Chris Hemsworth). However, when the Avengers time-traveled to retrieve the Tesseract, they encountered 2012 Loki. He stole the Space Stone and used it to escape getting arrested, which paves the way for Hiddleston's upcoming Loki-centric show.

Aside from his appearances in the MCU, Hiddleston starred on AMC's "The Night Manager," which earned him a Golden Globe win for best performance by an actor in a limited series or motion picture made for television.

He also starred in 2017's "Kong: Skull Island" with MCU costars Brie Larson and Samuel L. Jackson.

Hiddleston made his Broadway debut in 2019 with "Betrayal," which he starred in with Charlie Cox (who portrayed comic-book character Daredevil in a Netflix series).

He was a scientist who first met Tony Stark on New Year's Eve in 1999 and pitched the idea for Advanced Idea Mechanics (AIM). Tony brushed him off and years later, Aldrich reached out to Stark Industries with the idea to alter human DNA through an experiment called Extremis.

Pepper Potts (Gwyneth Paltrow) decided against it because it had the potential to be used as a weapon, and Aldrich later injected her with Extremis to manipulate Tony into working with him on the project. Pepper killed him during the film's major battle scene.

He starred as Dr. Emil Harting in "Bloodshot," a movie led by Vin Diesel and based on characters from Valiant Comics.

After appearing in the MCU, Pearce starred alongside fellow Marvel star Cobie Smulders in the 2015 movie "Results" and appeared in the sci-fi movie "Results" with Kristen Stewart and "X-Men" star Nicholas Hoult.

The actor also portrayed iconic author F. Scott Fitzgerald in the 2016 movie "Genius" and appeared as Peter Weyland in 2017's "Alien: Covenant." You may have seen him on Netflix's "The Innocents," "Mary Queen of Scots," and FX's miniseries called "A Christmas Carol."

In 2016, the actor welcomed a son named Monte Pearce with "Game of Thrones" star Carice van Houten, who he met on the set of the 2016 movie "Brimstone."

He planned on using the power of the Aether to spread darkness over the Nine Realms so the Dark Elves could take over. Thor and Jane Foster (Natalie Portman) sent Malekith to Svartalfheim, where he was subsequently crushed to death by his own ship.

After starring in the "Thor" sequel, he appeared on shows like "Safe House" and "The Leftovers," in addition to a few TV movies.

In the decades after Hydra found Bucky, he assassinated more than 200 people for the organization, including Tony Stark's parents.

Steve Rogers/Captain America teamed up with Sam Wilson/Falcon (Anthony Mackie) and Natasha Romanoff/Black Widow (Scarlett Johansson) to stop the mysterious assassin. But things got complicated when he learned that the foe was actually Bucky, his best friend who he believed died in the first "Captain America" movie.

Robert Redford's Alexander Pierce and Frank Grillo's Brock Rumlow/Crossbones also served as antagonists in the movie.

After "The Winter Soldier," Stan reprised his MCU role for an end-credits scene in "Ant-Man," followed by an appearance in "Captain America: Civil War," fighting alongside Cap.

Bucky went on to show up in the end-credits scene of "Black Panther," as the character was still recovering in Wakanda. Stan has since starred in "Avengers: Infinity War" and "Avengers: Endgame."

The actor has also starred in "I, Tonya" with Margot Robbie, "Destroyer" with Nicole Kidman, and "Endings, Beginnings" with Shailene Woodley.

Next, he'll star in "The Devil All the Time" (based on a book of the same name by Donald Ray Pollock) with Tom Holland, Robert Pattinson, and Bill Skarsgard. The movie hits Netflix on September 16, 2020.

Ronan was the person responsible for the death of Drax's (Dave Bautista) family members. The Guardians used the power stone to kill Ronan near the end of the 2014 film.

Pace is no stranger to major movie franchises. He also starred as Garrett in the final "Twilight" movie and played Thranduil in the "Hobbit" films.

In addition, the actor guest-starred on "The Mindy Project" and starred on the AMC show "Halt and Catch Fire."

Ultron's program was created by Tony, with the intention of being a peacekeeper that protected Earth from threats. But when Ultron deemed humans to be the source of the threat, he took violent action.

"Age of Ultron" also introduced fans to two additional antagonists: Baron Von Strucker (Thomas Kretschmann) and Ulysses Klaue (Andy Serkis). The latter character lost his arm during an argument with Ultron and returned with a new prosthetic one in "Black Panther."

He's starred on the show since it premiered in 2013. In February 2020, the show got renewed for an eighth season.

Hank Pym (Michael Douglas) was Darren's mentor.

Darren wore his Yellowjacket suit during his fight with Ant-Man/Scott Lang (Paul Rudd) and was defeated when the superhero went sub-atomic.

You may have also seen the actor on dramas like "House of Cards," "Girls," and "The Strain." Stoll portrayed real-life astronaut Buzz Aldrin in the 2018 movie "First Man," which starred Ryan Gosling as Neil Armstrong.

Zemo was motivated by the death of his family members in Sokovia due to the destruction caused by the Avengers in "Age of Ultron." He also used Hydra's Winter Soldier Book to manipulate Bucky Barnes/Winter Soldier.

In the 2016 movie, the character successfully managed to incite an all-out war with the Avengers taking sides (Team Captain America versus Team Iron Man) and fighting each other.

Brühl was seen as Zemo in a TV spot for Marvel's upcoming Disney Plus shows. The actor also shared photos of himself in character on Instagram, including an image that showed him wearing the comic-book character's signature mask.

Outside of the MCU, Brühl also stars as Laszlo Kreizler on TNT's "The Alienist" and will appear in the upcoming "Kingsman" prequel.

He was established as the movie's villain during the opening scene after he stole a page from the Book of Cagliostro with the intention of bringing the Dark Dimension to Earth.

To protect the planet, Doctor Strange (Benedict Cumberbatch) negotiated with Dormammu and sent Kaecilius to the Dark Dimension.

Since starring in "Doctor Strange," the "Hannibal" actor has appeared in movies like "At Eternity's Gate" and "Polar."

Next, he'll star in a dystopian film called "Chaos Walking" with Tom Holland, Nick Jonas, and Daisy Ridley.

He was a Celestial and the biological father of Peter Quill/Star-Lord (Chris Pratt).

Ego's plan was to carry out "The Expansion," but Peter defeated him by tapping into his own Celestial powers and destroying Ego's planet with a bomb set off by Groot.

The same year that the "Guardians" sequel was released, Russell starred as Mr. Nobody in "The Fate of the Furious."

The actor also portrayed Santa Claus in the 2018 Netflix movie "The Christmas Chronicles" alongside longtime partner Goldie Hawn (as Mrs. Claus) and his stepson, Oliver Hudson. Russell and Hawn will reunite on-screen for an upcoming "Christmas Chronicles" sequel.

He was a disgruntled salvage worker who cleaned up after the chaos caused by the Chitauri invasion in New York in "The Avengers." Years later, Adrian and his crew used Chitauri tech to build weapons (including his Vulture suit).

In the movie's plot twist, he turned out to be the father of Liz (Laura Harrier), the popular girl at school who Peter Parker (Tom Holland) had a crush on.

Spider-Man saved Vulture from dying during their big fight and Adrian ended up getting arrested.

Keaton portrayed the DC comics character in two "Batman" movies released in 1989 and 1992. According to The Wrap, the actor's role in the upcoming film isn't guaranteed or confirmed yet, but possible as part of the multiverse.

After starring in "Spider-Man: Homecoming," Keaton appeared in the 2017 action movie "American Assassin" with "Teen Wolf" alum Dylan O'Brien.

He also played the villain V. A. Vandevere in Disney's 2019 live-action remake of "Dumbo."

She was Odin's (Anthony Hopkins) first-born child and referred to as the "goddess of death." Hela, who was released from prison after her father's death, was so powerful that she was able to destroy Thor's hammer. Thor lost his eye during a confrontation with Hela, which resulted in him wearing an eye patch (just like Odin).

Hela was killed by Surtur during his destruction of Asgard.

Since "Ragnarok," the "Lord of the Rings" alum has kept busy with roles in movies like "Ocean's Eight" with Sandra Bullock and "Where'd You Go, Bernadette" with "Pretty Little Liars" star Troian Bellisario.

Blanchett also voiced characters in "How to Train Your Dragon: The Hidden World" and "Mowgli: Legend of the Jungle."

Jordan, who accepted the role in Ryan Coogler's movie before he even read the script, dove headfirst into his role as a complex antagonist — and it paid off. His character briefly dethroned Wakandan leader and cousin T'Challa/Black Panther (Chadwick Boseman), but Jordan made Killmonger someone that audiences could feel a degree of sympathy for.

He became an assassin in the years after his father was murdered by T'Chaka (John Kani) and was fueled not only by vengeance but by a desire to use Wakanda's resources to help the rest of the world. Though he turned to violent measures, Killmonger was a refreshing and intriguing villain.

His final moments in the film were also profound.

After being stabbed by T'Challa, Killmonger chose to die while watching the sunset in Wakanda (which his father always told him were "the most beautiful in the world"), rather than live and be a prisoner in the nation.

To date, Jordan has played two comic-book characters: Killmonger in "Black Panther" and Johnny Storm/Human Torch in a critically-panned "Fantastic Four" reboot.

After "Black Panther," the actor starred in HBO's film adaptation of Ray Bradbury's classic dystopian novel "Fahrenheit 451." He then reprised his role as Adonis Johnson for "Creed II" with Sylvester Stallone. Jordan served as an executive producer for both projects.

Jordan also produced and starred in 2019's "Just Mercy," whose cast included Jamie Foxx and Marvel's Brie Larson. Jordan portrayed real-life civil rights defense attorney Bryan Stevenson in the movie.

Ava's father, Elihas Starr, and Hank Pym were S.H.I.E.L.D. colleagues who worked on quantum research. After being fired by Hank, Elihas did independent research and one experiment went wrong. It led to the death of Ava's parents, while she was left with powers that enabled her to phase through objects and people (also known as "molecular disequilibrium").

The show, released on NBCUniversal's new streaming service called Peacock in July, also stars "The Vampire Diaries" alum Joseph Morgan. John-Kamen plays Wilhelmina "Helm" Watson, a gender-flipped version of the novel's Helmholtz Watson.

Since the "Ant-Man" sequel, the actress has also starred on shows like "Killjoys" and "The Stranger."

Captain Marvel (Brie Larson) defeated him after tapping into the true extent of her powers. Then she sent him back to Hala, the homeland of the Kree.

The "Harry Potter" franchise has been surrounded by controversy, but a third "Fantastic Beasts" movie is still in the works.

Aside from that, Law also starred in "The Rhythm Section" with Blake Lively and earned a Golden Globe nomination for his role on "The New Pope."

Six stones (mind, time, power, soul, space, and reality) were spread throughout the universe at different times and the Titan tracked them down during the MCU's first three phases.

In 2018's "Avengers: Infinity War," Thanos snapped half of the universe out of existence after acquiring all the stones.

At the start of 2019's "Avengers: Endgame," the remaining superheroes found Thanos and Thor decapitated him. Then, they traveled back in time to regain the Infinity Stones and bring back the people who disappeared in "Infinity War." In the film's major battle scene, superheroes across the universe united to fight Thanos from 2014.

Tony Stark snapped away Thanos and his army by wielding his own gauntlet, at the expense of his own life.

The movie also stars Zendaya, Timothée Chalamet, and "Aquaman" star Jason Momoa, among many other notable actors. It's scheduled for release on December 18, 2020.

Peter Parker/Spider-Man formed a friendship with Quentin as they teamed up to fight Elementals — which turned out to be illusions created by the sneaky character so he'd look like a hero.

Unlike the fake backstory Quentin gave Peter, he was actually a malicious former employee at Stark Industries who held a grudge against Tony.

Quentin died at the end of the film, but not before recording and releasing a video exposing Peter as Spider-Man. Quentin also manipulated footage to fool everyone into thinking that the web-slinger was behind the destruction in London.

He starred in the play with Tom Sturridge. The show was originally performed off-Broadway prior to its Broadway run from August to September 2019.

More recently, Gyllenhaal produced the horror movie "Relic."

He also serves as a producer on the upcoming film "The Devil All the Time," which hits Netflix in September 2020 and stars Holland, fellow MCU actor Sebastian Stan (Bucky Barnes), and Robert Pattinson.