Robert Downey Jr. Films Ranked Worst to Best

adminMarch 16, 2021

Robert Downey Jr. Films Ranked Worst to Best

Robert Downey Jr. is one of the most undeniable movie stars working today, but how do his films rank from worst to best? From his career start in the Brat Pack, to his Academy Award-nominated turn in Chaplin, to his ascension to screen royalty as the Godfather of the Marvel Cinematic Universe, his filmography is brimming with ups and downs.

The actor started young, but burst fully onto the scene in 1997’s Less Than Zero, beginning a career that reached an early peak with his unanimously-praised turn as Charlie Chaplin in 1992. Soon after, he hit rock bottom after struggling with drug addiction for much of his life, eventually landing in state prison. Vowing to rehabilitate himself and turn his life around, Downey soon picked right back up where he left off, turning in a slew of fantastic performances in interesting films before exploding into the stratosphere as the MCU’s Iron Man.

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Related: Robert Downey Jr. Changed The MCU With An Improvised Iron Man Line

His story is its own superhero origin tale, one of overcoming struggles and reaching for the stars. While he’ll always be remembered as Iron Man, there are 50-some other roles that are worth a look. Here are the actor’s major films, ranked from worst to best.

59. Dolittle

This Downey-led update on Hugh Lofting’s popular children’s book series is a thoroughly inept stinker, and one of the worst films of 2020. After a troubled post-production process, the resulting film strands an incomprehensible Robert Downey Jr. in the midst of a personality-devoid squad of CGI animals. It’s chaotic, confusing, and ultimately mind-numbingly boring.

58. Johnny Be Good

Robert Downey Jr Johnny Be Good movie

Boasting that rarest of things, a zero-percent rating on Rotten Tomatoes, this comedy about a high school quarterback being courted by a bunch of elite colleges who ply him with everything a teenage boy could possibly want gives “sophomoric” a whole new name. Crass, stupid, and entirely pointless, this Anthony Michael Hall-led vehicle is like a John Hughes film if the writer/director lost all sense of taste.

57. Friends and Lovers

Downey plays a German ski instructor in this wildly unfunny 1999 sex farce. It’s the only movie its director George Haas ever made, and for good reason; this is a film with the sense of humor of a 13-year-old schoolboy and an emotional perception to match.

Related: Robert Downey Jr. Is Right, Iron Man’s Story is Finished

56. Air America

Air America is a sort of ’90s cocktail of the wise-cracking war comedy of MASH with the bro-comedy aesthetics of Top Gun, with none of the humanity of the first or the style and fun of the second. The movie star wattage of Robert Downey Jr. and his partner Mel Gibson is strong; unfortunately, their chemistry is not.

55. Gothika

Gothika - Robert Downy Jr and Halle Berry

Gothika is remembered mostly (if at all) as the bad horror movie Halle Berry made after winning an Oscar, and for good reason. This puzzling thriller about a psychiatrist imprisoned in her own mental hospital and accused of the murder of her husband is hampered by a convoluted plot and a bizarre tone that mixes typical mystery tropes with a smattering of bizarre supernatural elements. The result is a confusing mess that not even Berry or Downey can rescue.

54. Tuff Turf

Before Age of Ultron, James Spader and Robert Downey Jr. co-starred in this sorry excuse for a teenage exploitation film. Attempting to harness the spirit of John Waters but lacking any of the tonal cohesion of that Master of Camp, Tuff Turf settles for a confused style somewhere at the cross-section of coming-of-age story and beach party musical, leaving its stars hung out to dry in the process.

53. Too Much Sun

Robert Downey Jr Too Much Sun

Robert Downey Sr. directed this tasteless comedy about the gay son (Eric Idle) and lesbian daughter (Andrea Martin) of a wealthy tycoon who are to be disinherited if they can’t produce an heir within a year of their father’s death. This 1991 “comedy” is riddled with outdated gay-bashing from top to bottom, equating homosexuals with pedophiles and even making AIDS jokes.

Related: Enola Holmes: How Henry Cavill’s Sherlock Compares To Robert Downey Jr.

52. In Dreams

Robert Downey Jr Annette Bening In Dreams (1)

Downey plays a serial killer with a psychic connection to Annette Bening in this cerebral thriller. Directed by Neil Jordan, the film boasts plenty of lush visuals, but not much in the way of a coherent plot. It’s ultimately probably too heady for the horror crowd and too shallow for those wanting a more interesting genre exercise.

51. U.S. Marshals

This unnecessary sequel to The Fugitive sees Tommy Lee Jones returning to his Academy Award-winning role of U.S. Marshal Sam Gerard with diminishing returns. Playing mostly as an uninspired remake of the first, with Wesley Snipes in the Harrison Ford role and Robert Downey Jr. as Jones’ partner, the film offers little but memories of its far superior predecessor.

50. The Shaggy Dog

Robert Downey Jr. In Disney's The Shaggy Dog

This retread of the 1959 Disney original is a totally harmless bit of fluff that unfortunately also lacks any sense of inspiration or wit. This time, Tim Allen plays the attorney-turned-pooch in a film that utterly wastes its stacked supporting cast, which aside from Downey also features Danny Glover and Kristin Davis.

49. Lucky You

Lucky You

Lucky You is a high-stakes, low-ambition rom-com in which Eric Bana has to win Drew Barrymore and a world championship poker game in Las Vegas. Downey plays Bana’s father and the poker legend he ultimately has to face at the table, in this breezy, mildly-charming, if forgettable cash-in on America’s late-2000’s obsession with poker.

Related: What Is Robert Downey Jr’s Net Worth?

48. Hugo Pool

Another Robert Downey Sr. enterprise, this quirky love story centers on the romance between a pool cleaner and one of her clients who has ALS, played by Patrick Dempsey. As irreverent as any of the underground filmmaker’s offerings, with several failed attempts at heartfelt sincerity, Hugo Pool drowns most of its cast in the deep end. The lone exception might be Downey Jr., who is bizarrely captivating (if a bit over-cooked) as an eccentric film director.

47. One Night Stand

Mike Figgis directs this film about a man, played by Wesley Snipes, who commits adultery on a trip to New York City while visiting his friend, a gay man suffering from AIDS. This drama doesn’t really have the bite or sensuality one might hope, but it does boast some extremely good performances, most of all Downey, who brings a soulful sensitivity to the potentially cynical and awards-baiting role of the sick friend.

46. Fur: An Imaginary Portrait of Diane Arbus

This fictionalized take on the extraordinary artist Diane Arbus, who sought to give representation to marginalized groups through her photography, sees her falling in love with her new neighbor, an enigmatic man with hypertrichosis, a condition characterized by an abnormal amount of hair growth on the body. Nicole Kidman plays Arbus, Downey the neighbor, and together they bring a believable watchability to a film that otherwise could be seen as head-scratchingly bizarre.

45. Eros

Eros is a bizarre entry; an anthology film with three parts directed by three different and incredible-in-their-own-right directors: Wong Kar-Wei, Steven Soderbergh, and Michelangelo Antonioni. While the Wong Kar-Wei entry is the most haunting and memorable of the film, Downey commands the screen as a neurotic client of a psychiatrist, rambling and riffing as only he can in the Soderbergh sketch “Equilibrium.”

Related: Perry Mason: Why Matthew Rhys Replaced Robert Downey Jr. In HBO’s Reboot

44. Firstborn

Director Michael Apted brings his typical empathy and compassion to this story of a teenage boy protecting his mother from her abusive drug-dealing boyfriend. Indeed, all the performances here are stellar, from Teri Garr as the mother to Downey himself as her son. It’s unfortunate, then, that the whole film ultimately devolves into little more than movie-of-the-week heavy-handedness about drugs destroying suburban life.

43. Black and White

James Toback’s sprawling and ambitious mess of a film centers on a documentary filmmaker (Brooke Shields) turning her camera on the infiltration of hip hop culture into the white mainstream. There’s a lot of interesting ideas at work here, and a stellar performance by Downey once again playing a gay man, his best scene here being one where he makes a flirtatious advance on Mike Tyson.

42. The Singing Detective

Downey plays a hospitalized dimestore novelist who imagines he’s one of the detectives from his books in this ambitious and utterly bizarre 2003 update of the 1987 television miniseries. The actor’s phenomenal performance goes a long way, and there’s a lot of style on display here, but ultimately the film’s slapdash style, moving from noir action beats to goofy lip-synched musical numbers, becomes a bit overwhelmingly grating.

41. Due Date

Zach Galifianakis and Robert Downey Jr in Due Date

This follow-up to Zach Galifianakis’ Hangover slam-dunk and Downey’s newfound Iron Man celebrity is typical of director Todd Phillips’ worst impulses, trading in comedy for crassness and mean-spiritedness for any sense of warmth or humanity. There are a few laughs, but mostly this road movie is lesser work from both these actors.

Related: The Iron Man 1 Scene That Has a Hidden Robert Downey Jr. Meaning

40. The Judge

Robert Downey Jr in The Judge

Robert Duvall got a surprise Oscar nomination for this cliché drama about a shady attorney with daddy issues who takes on his father’s defense after he’s arrested for a hit-and-run. Downey, however, is arguably the best part of a film that seemingly has no reservations flitting from overly-sentimental family drama to remarkably un-thrilling courtroom procedural.

39. Two Girls and a Guy

James Toback’s dark comedy about two women who confront the two-timing actor who’s professed his love to both is a lively but indulgent roller-coaster ride that’s saved by a seductively compelling performance by Downey. The versatile actor brings a creeping complexity to this snake of a character, and the result is undeniably watchable.

38. Only You

Moonstruck director Norman Jewison returns to the romantic comedy well with less thrilling, though still charming, results, this time pairing Marisa Tomei with Robert Downey Jr. Unabashedly sentimental and only slightly cloying, Only You coasts on the two leads’ chemistry and Jewison’s gorgeous travelogue photography of Italian vistas.

37. Weird Science

Downey’s first real film role was as jock bully Ian in this odd John Hughes movie based on an obscure comic about two high school nerds who Frankenstein their dream woman to life. Without a doubt one of Hughes’ lesser works, scrappily put together and also cringey in its high-school-boy sensibility. There’s still enough of the writer-director’s signature warmth and buoyancy, but much of this film just turns out fairly questionable.

Related: Wait, Why Does Robert Downey Jr’s Dolittle Movie Have a Dragon?

36. 1969

Robert Downey Jr 1969 movie

A young Downey Jr. and Kiefer Sutherland star as two young men coming of age in the turbulent decade of the 1960s, experimenting with drugs and becoming embroiled in the anti-Vietnam War movement. There’s nothing too remarkable on display here, but this is still a fairly affecting drama with a performance from Downey that would tease the phenomenal career to come.

35. The Pick-Up Artist

Downey’s first collaboration with James Toback is an overly-silly film about a serial commitment-phobe who meets his match with Molly Ringwald’s spunky tour guide. Ringwald and Downey are really the only reason to watch this one, with the latter displaying such lighthearted charm that it almost makes up for the fact his character is a total jerk.

34. Charlie Bartlett

Downey’s last-released film before Iron Man shot him into absolute superstardom, Charlie Bartlett is a John Hughes-wannabe about an awkward high school student who becomes a one-man psychiatric service and pharmaceutical company. The film ultimately lacks Hughes’ inspiration and can’t decide if it’s a snarky comedy or a bizarre antihero story, but the performances are fantastic, particularly Downey’s as an alcoholic high school principal and the late Anton Yelchin, who is effervescently lovable as the titular Charlie.

33. The Gingerbread Man

Robert Downey Jr. is particularly sleazy as a boozy private eye, but the real draw here is the bizarre marriage of Robert Altman directing a John Grisham story. The actual plot is not all that interesting, but Altman’s direction is as much a master-class as ever, and while the dialogue floats in one ear and out the other, the visual storytelling is consistently evocative and memorable.

Related: Why Robert Downey Jr’s First Post MCU Role is Dr. Dolittle

32. Game 6

Nine years before Birdman, Michael Keaton played another anxious Broadway actor worried about a negative review from a critic, this time played by Downey himself. Written by Don DeLillo, this quirky comedy takes great delight in showing its pen, to mixed results. However, the actors are having a blast, and Keaton and Downey strike a wickedly adversarial dynamic.

31. Sherlock Holmes: A Game of Shadows

Holmes and Watson in Sherlock Holmes A Game of Shadows

Guy Ritchie’s second Holmes adventure repeats the original’s eschewing of the simple charm of Sherlock’s deductive reasoning for blockbuster action and turns it up to a fever pitch of button-mashing video game-style histrionics. Downey is still having fun here, but the film’s manic “everything but the kitchen sink” sensibility quickly veers into the realm of tedium.

30. Chances Are

Dirty Dancing director Emile Ardolino’s bizarre but charming Chances Are sees Christopher McDonald’s death and reincarnation as Robert Downey Jr. two decades later. Playing a young writer, Downey falls in love with Mary Stuart Masterson’s Miranda Jeffries, his daughter in his past life. As creepy as it all sounds, the screenplay by Mystic Pizza writers Randy Howze and Perry Howze keeps a light touch and a sense of fun throughout, and Downey anchors the whole thing with a solid early performance.

29. Restoration

Downey shines as royal physician Robert Merivel, who’s shunned from King Charles II’s court and leads the charge in helping Londoners suffering from the plague, all the while falling in love with the destitute Katherine, played by Meg Ryan. A meandering script is given a first-class polish thanks to stunning production design and an all-star cast which also features Sam Neill, David Thewlis, and Ian McKellen.

Related: Robert Downey Jr. Has Only Done 5 Non-Marvel Movies in The Last Decade

28. The Soloist

This inspirational story of how a disillusioned writer and a homeless virtuoso violinist change each other’s lives initially seemed like overly-sentimental Oscar-bait. Indeed, it doesn’t avoid all those trappings, but when it does it’s solely due to the performances of Jamie Foxx and especially Robert Downey Jr., who’s a smart enough actor to know that understatement is the way to make this material truly sing.

27. Iron Man 2

Tony and Rhodey in Iron Man 2

The Marvel Cinematic Universe is by now a well-oiled machine, but in 2010 the growing pains of the franchise were on full display in Iron Man 2, which trips over the momentum of its predecessor and all but faceplants. Downey is in fine enough form, but he’s constantly sidelined by a screenplay that would rather spend its time inelegantly setting up a bunch of other movies. Even Mickey Rourke, fresh off his career-best turn in The Wrestler, seems to be phoning things in, ceding the role of scene-stealer to Sam Rockwell, who as Justin Hammer is the main reason to rewatch this middling entry.

26. Avengers: Age of Ultron

After the high-flying fun of the first Avengers film, the franchise sputters with a considerably less inspired second entry. By this point, Downey could do this in his sleep, far enough removed from the inspiration of his entrance as Iron Man and the revitalization that would come with his character’s climactic moments in Endgame. It also doesn’t help that Ultron is among the MCU’s most lackluster villains (and that’s saying something), or that Joss Whedon seems to struggle to find a way to balance the film’s unwieldy cast as brilliantly as he did in its predecessor.

25. A Guide to Recognizing Your Saints

First-time director Dito Montiel adapts his memoir of the same name for the screen. Downey and Shia LaBeouf both play Dito, Downey as the older incarnation visiting his dying father and LaBeouf as the younger, growing up in a violent neighborhood in Queens. The actor is plenty soulful in the adult timeline, but it’s the flashbacks that bring life to the film, filmed with a verite realism and acted by LaBeouf and an exceptionally good Channing Tatum.

Related: Why WandaVision Is About Iron Man’s Biggest Success and His Worst Failure

24. Spider-Man: Homecoming

Downey plays mentor (seemingly only half-checked-in) in this MCU retread of Spider-Man. It’s a bright, cheerful film, and Holland is perfectly charming, even if the whole thing seems over-eager to show the iconic hero as a youthful high-school boy. None of the grandiose fun of the first two Sam Raimi adventures is on display here, nor any attempt to recreate their pure bravura filmmaking style, but this is still a pleasant enough initial outing.

23. Back to School

This iconic Rodney Dangerfield vehicle about an uneducated self-made millionaire who enrolls himself in school to try and motivate his son features Downey in one of his first roles as Dangerfield’s son’s roommate, Derek Lutz. It’s a fun performance, shot concurrently with his one-season run on Saturday Night Live, and (interestingly enough) it’s the basis for Tony Stark’s de-aged appearance in Captain America: Civil War.

22. True Believer

Robert Downey Jr. and James Woods play a pair of lawyers who uncover a massive conspiracy after taking on a murder case in this engaging courtroom drama. Downey’s solid as the straight man, but this is the James Woods show from beginning to end, and director James Ruben surrounds him with a grounded foundation for him to let it rip, spinning his wheels with gleeful abandon.

21. Home For the Holidays

Jodie Foster directs and Holly Hunter stars in this all-too-real depiction of the chaos of a holiday spent with family. Downey employs the typically sensitive and three-dimensional touch he always has brought to the gay characters he’s played, and the film was repaid with a GLAAD Media Award nomination for Best Film.

Related: Superman & Lois’ Luthor Is An Anti-Superman Iron Man Clone

20. Captain America: Civil War

Iron Man and Captain America get into a bit of a squabble about government oversight in this post-Age of Ultron, pre-Infinity War installment in the Marvel Cinematic Universe. There are some interesting ideas here, plenty of big set-pieces, and Downey is fine as ever, but while the Russo Brothers tick all the boxes of what was expected in these offerings by this point, there’s significantly less personality on display here than in Iron Man or The Avengers. 

19. Soapdish

This backstage farce about the on-and-off-camera shenanigans around a soap opera features a wildly funny Downey as a producer scheming with an ambitious blonde to get her a bigger part by writing off the program’s leading lady. Riotous chaos follows, bolstered by a zany cast that includes Carrie Fisher, Cathy Moriarty, Sally Field, Whoopi Goldberg, and Kevin Kline in a Golden Globe-nominated performance as an actor returning to the show after his character has been beheaded.

18. A Scanner Darkly

One of director Richard Linklater’s most underrated efforts, A Scanner Darkly is a paranoia-riddled adaptation of the Philip K. Dick novel about a narcotics cop becoming an addict when he goes undercover in a futuristic society. Utilizing a rotoscoped technique nicely complements Downey’s animated acting style, and his explosively fun performance clashes well with the detached blankness of Keanu Reeves’ cop.

17. Richard III

Robert Downey Jr. plays Lord Rivers, one of the scheming Richard’s multiple victims in this update on the Shakespearean classic that resets the play in 1930s London. One of the best modern updates of a Bard text, the film is thrillingly anchored by Ian McKellen in one of his greatest performances as the murderous hunchback.

Related: The Arrowverse Is Making Superman Just Like the MCU’s Iron Man

16. Avengers: Infinity War

Robert Downey Jr as Tony Stark in Avengers Infinity War

The Russo Brothers’ bombastic Infinity War takes the multiple superheroes approach of the original Avengers and ups the ante by throwing nearly every Marvel Cinematic Universe character into the mix and letting them bounce off each other for nearly three hours. The result is certainly fun for fans, but also frustratingly slight; with so many characters, there’s not enough time with any of them to really focus or care. Of course, it all comes down to the Thanos snap heard round the world, a climactic moment that decimates half the cast and renders the villainous Thanos victorious. Even if the audience knows everyone will be coming back in the next installment, Downey plays the tragedy of seeing his friends vanish beautifully.

15. Avengers: Endgame

Iron Man Snaps Infinity Gauntlet in Avengers Endgame

No amount of criticism could stop the MCU’s rabid fans from loving every minute of this climactic installment, which is as much a warm hug from Kevin Feige and company as it is a finale to this cycle of the franchise. It’s true the first two hours are overstuffed with fan service and hand-wavey time travel shenanigans, but the return of the lost Avengers through the portals, led by the late Chadwick Boseman’s Black Panther, is the type of rousing blockbuster moment for which people go to the movies. Of course, Downey’s final scene as Iron Man is the icing on the cake, a fitting farewell to a character which birthed a franchise and reignited a career.

14. Less Than Zero

Robert Downey Jr as Julian Wells in Less Than Zero

The film that made Robert Downey Jr. a star, Less Than Zero is an adaptation of a Brett Easton Ellis book about the paths three rich best friends take after graduating high school. Downey is a revelation as the drug-addicted Julian, laying the gauntlet for a career that would always find the most humane, sensitive way to portray struggling and marginalized characters.

13. Sherlock Holmes

Robert Downey Jr and Eddie Marsan in Sherlock Holmes

The first film Downey signed onto after the success of Iron ManSherlock Holmes is Sir Arthur Conan Doyle by way of Guy Ritchie, which is to say that subtlety and deductive reasoning are out the window and CGI-filled action sequences are in. That said, there’s plenty of fun to be had here and Downey, the recently-revitalized actor, proves he’s more than capable of holding down two massive franchises, in a performance that won him a Golden Globe.

Related: What Iron Man Learned From Every Avenger

12. Good Night, and Good Luck

The best film in George Clooney’s directing ouvre is the engrossing portrait of CBS newscaster Edward R. Murrow’s battle against Senator Joe McCarthy and the Communist blacklist. Downey Jr. rounds out an ace cast with a pathos-filled performance as a CBS employee whose career is put in jeopardy as he struggles to keep his marriage to one of his coworkers a secret.

11. Bowfinger

An underrated gem of a comedy from director Frank Oz, Bowfinger is the story of filmmaker Bobby Bowfinger (Steve Martin), who’s given the green light on a schlocky sci-fi film if he can land A-lister Kit Ramsey (Eddie Murphy). This forces Bowfinger to shoot the film without Ramsey realizing he’s in it, and hilarity ensues. Downey plays the slimy producer who sets the whole thing in motion, making the most of his limited, but hysterical, screen time.

10. Iron Man 3

Iron Man 3 Tony Stark

Perhaps the most underrated entry in the entire Marvel Cinematic Universe, this Shane Black-helmed entry picks up the torch passed on by mega-hit The Avengers and promptly tosses it over its shoulder and decides to just do its own thing. Freed from the burden of playing housekeeping on the myriad other properties in the MCU, Iron Man 3 makes the wise choice to focus on the character that got everyone invested in the first place, Tony Stark himself, as he wrestles with the notion of scaling back his role as Iron Man and focusing more on his personal life. It is also, for those who practice, a Christmas movie.

9. Kiss Kiss, Bang Bang

Iron Man is often cited as the movie that announced the triumphant revitalization of this always-stellar actor’s career, after decades in and out of rehab and time served in state prison. However, it was Shane Black’s twisty-turny directorial debut that undoubtedly set the stage. Downey is on fire as a thief posing as an actor researching a part, and his chemistry with Val Kilmer as homosexual detective Gay Perry practically explodes off the screen. Dripping with irony as it gleefully dances through its convoluted plot, Kiss Kiss, Bang Bang sees Downey returning to the screen ready to have some real fun.

Related: Endgame Would’ve Been Better Switching Key Iron Man/Captain America Moment

8. The Avengers

There’s something so gloriously old-fashioned about this, the first Avengers movie. A Dirty Dozen-esque, “let’s get the gang together” style blockbuster, this magnificent crowd-pleaser hits all the right notes and sends its audience on a rollercoaster ride of pure nerdy joy. Perhaps it’s because there’s a human element at play, with Nick Fury (and Clark Gregg’s heartfelt Phil Coulson) trying his damnedest to make this super-team work; perhaps it’s because Joss Whedon draws each of these characters so clearly and specifically; perhaps it’s because the formula wasn’t set yet, and there was just such joy in seeing all these actors interacting with each other. Whatever the reason, the Avengers have never been as pure, as fun, as perfect an embodiment of the power of escapist entertainment as they were when they first assembled.

7. Short Cuts

Robert Altman’s sprawling 1993 passion project, Short Cuts uses the writings of short story author Raymond Carver to try to recapture the epic, ensemble magic of his masterpiece Nashville and, shockingly, succeeds. Downey plays Bill Bush, a makeup artist and one of 22 main characters, all Los Angeles residents dealing with life, love, and death, and all of them treated with more clarity and specificity than the unwieldy ensembles of the latter MCU offerings.

6. Natural Born Killers

Wayne Gale Robert Downey Jr. Natural Born Killers

Released like a bomb went off in 1994, Oliver Stone’s Natural Born Killers based on a story and screenplay by Quentin Tarantino, is packed to the brim with gory, cartoonish violence and over-the-top style. Robert Downey Jr. chews the scenery to haunting and captivating effect as a television journalist obsessed with the trail of carnage left by Mickey and Mallory Knox (Woody Harrelson and Juliette Lewis). It’s an acquired taste for sure, but its brutal satire of a culture obsessed with violence is undeniable.

5. Wonder Boys

Curtis Hanson’s marvelous film adaptation of Michael Chabon’s true-to-reality book about life on campus is achingly authentic while still being as charming and winning a crowdpleaser as anyone could possibly want. Robert Downey Jr. was on probation when filming was about to commence but committed for the four-and-a-half month shoot, and the result is a fantastic performance rounding out an ensemble that includes career-best turns from Tobey Maguire, Frances McDormand, and Michael Douglas.

Related: The DCEU Must Avoid Making Batman Its MCU Iron Man Clone

4. Zodiac

Jake Gyllenhaal and Robert Downey Jr sitting in Zodiac

One of David Fincher’s most underrated masterpieces explores the unsolved Zodiac murders of the ’60s and ’70s through two interweaving stories: the first, about a reporter and a cartoonist who become obsessed with the case, and the second about two cops tracking down the killer. Pre-MCU Downey, Jake Gyllenhaal, and Mark Ruffalo all give phenomenal performances, particularly Downey, whose unraveling alcoholic is a haunting portrait of the fatigue that accompanies obsession. Of course, the real star is Fincher, whose disciplined filmmaking creates a work of focus and intent so filled with dread it’s unforgettable.

3. Tropic Thunder

Downey’s controversial role in Tropic Thunder as method actor Kirk Lazarus, who never breaks character until he’s recorded a film’s DVD commentary and decides to surgically don blackface to play an African-American Vietnam sergeant, has come under reevaluation lately as to whether or not it’s offensive. However, director Ben Stiller and Downey are incredibly clear in their intent to not promote racist practices, but instead to skewer the method madness of actors whose ignorance goes hand-in-hand with their lust for Oscar glory. The Lazarus character is one of the most brutally satiric elements in this fantastic film, overall one of the more adventurous and bold studio comedies of the 21st century. Ironically, Downey was granted an Oscar nomination for Best Supporting Actor, a rarity for such an out-and-out comedic performance.

2. Chaplin

Before Tony Stark, this was the peak of this phenomenal actor’s career, an Oscar-nominated performance that not only resembles the legendary actor and director but manages to capture the ineffable playfulness, puckish sense of mischief, and sadness of Chaplin. The surrounding film, by Richard Attenborough, doesn’t necessarily rise above the usual biopic trappings, but Downey’s performance is impossible to resist, a turn that would’ve been the actor’s career highpoint were it not for what would come more than a decade later…

1. Iron Man

Iron Man Movie Robert Downey Jr Costume Helmet

Downey was back; after years of struggles with substance abuse led to rock bottom, he was rehabilitated and ready to reclaim his place as one of the most exciting and surprising actors working. Director Jon Favreau believed the performer would elevate the film with the same mixture of gravitas and fun that Johnny Depp brought to Jack Sparrow in Pirates of the Caribbean, but the result has proven even more iconic and long-lasting than that spectacular turn. This is a full-stop, no-holds-barred, movie-star performance, one that mixes the actor’s signature blend of humanity, snark, and bad-boy charm with triumphant results. Robert Downey Jr. had a full career before this, but when he said, “I am Iron Man” for the first time in 2008 audiences instantly believed him, and they haven’t stopped since.

Next: WandaVision Proves Iron Man Was Right About Scarlet Witch’s Threat

  • Black Widow (2021)Release date: May 07, 2021
  • Sherlock Holmes 3 (2021)Release date: Dec 22, 2021

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