I Play Rocky And The Best Actors-As-Actors Performances, Ranked
Just under 50 years since Rocky premiered, a new movie called I Play Rocky is stepping into the cinematic ring for the first time this month to tell the unlikely underdog story of how that iconic sports film was made.
Directed by Peter Farrelly (of Green Book fame), I Play Rocky is a heart-warming and knowingly meta tale of an Italian American underdog who punched above his weight to get into Hollywood, one lucky jab at a time. The protagonist, of course, is the star and writer of that 1977 Best Picture winner, Sylvester Stallone, and he’s played in an uncanny fashion by Anthony Ippolito — an up-and-coming star who also did a fine Al Pacino impression in the miniseries The Offer in 2022 and now looks set to garner plenty of attention as these year's awards season beckons.
That connection, between playing beloved actors and picking up gold plated hardware for your efforts, is one of the things that links many of the stars on our ranked list of actor-on-actor performances — that and the fact that the movies themselves aren’t always as strong as the portrayals. Whatever the case, here are our ten favourites of this fine Hollywood tradition.
10. Renée Zellweger as Judy Garland
As mentioned above, not all the great actors-on-actors performances come in what we’d necessarily call great movies; and even though Renée Zellweger’s performance as Judy Garland, the troubled star of The Wizard of Oz and A Star is Born, is impeccable, Judy itself is probably no more than a decent movie.
Zellweger did, however, win the Academy Award for Best Actress for her efforts — which maybe says as much about the kind of roles that sometimes win these prizes as the performance itself. The movie includes flashbacks to Garland’s earlier years in Hollywood but mostly takes place in 1968 and 1969, when the actress performed a number of one woman shows in London’s Talk of the Town theatre before dying of an overdose at the terribly young age of 47.
The movie comes alive mostly during Zellweger's depiction of Garland’s performances, for which Zellweger studied the actress's stage presence and singing voice (no overdubbing here) in order to fully embody the role. Impressive stuff.
9. Dane DeHaan as James Dean
James Dean is an actor who younger stars have been attempting to mimic ever since his whirlwind rise and fall — an 18-month period between 1955 and 1956 in which East of Eden, Rebel Without a Cause and Giant (his only real screen credits as an actor) were all released on either side of his fatal car crash.
In Anton Corbijn’s stylish, melancholy, black and white period piece, Life, Robert Pattinson stars as Dennis Stock, the Life magazine photographer who was assigned to take pictures of the up and coming actor — who is played wonderfully in the movie by Dane DeHaan.
To keep the portrayal as elusive as the actor himself, Corbijn keeps Dean and DeHaan’s performance on the margins of his movie and the results are quite affecting. As in real life, Stock, like everyone else, never quite managing to get a hold of his subject until it was too late.
8. Robert Downey Jr. as Charlie Chaplin
Long before his stint in rehab, his renaissance as Tony Stark in the MCU, and his Oscar win for Oppenheimer, Robert Downey Jr. landed his first nomination from the Academy for this unmistakably hard-earned performance as the silent era legend Charlie Chaplin in Richard Attenborough’s 1992 biopic.
The performance is remarkable for a number of reasons, not least for the fact that Downey went to trouble of learning not only Chaplin’s mannerisms and speaking patterns but also the iconic walk and some of the most famous stunts of his most beloved character, The Tramp.
On top of that, Downey picked up some tennis and violin skills — learning both with his left-hand in order to portray the working class English émigré as accurately as possible. If you’re a fan of what this actor has done in the last 20 years of movies, you owe it to yourself to go back and check this out.
7. Tom Burke as Orson Welles
It’s amazing to me that Tom Burke isn’t a household name already. From The Souvenir to Furiosa to Black Bag, Burke has brought gravitas and devilish charm to everything I’ve seen him in, although for some reason is always just a little outside of those movies' spotlights.
A great example of this is his memorable turn as Orson Welles in David Fincher’s Mank — a movie with the temerity to suggest that the writer and director of Citizen Kane was some kind of hack; but thankfully one packed with juicy performances from game actors.
Putting those suspicions to one side, Burke makes his presence felt in Mank with very little screen-time, which is saying a lot for a movie in which Gary Oldman seems determined to swallow up any piece of scenery that comes his way. If Fincher one day decides to make an Orson-focused sequel with Burke — maybe set it during the fiasco production of The Magnificent Ambersons? — I will be first in line.
6. James Franco as Tommy Wiseau
We should know better than to give James Franco an inch of copy these days, but his hilarious and loving portrayal of Tommy Wiseau in The Disaster Artist was arguably the best thing he did in his career — at least this side of Freaks and Geeks and Sam Raimi’s Spider-Man.
The Disaster Artist (which Franco also directed) tells the story of the making of The Room — a movie widely considered the worst of all time — from the perspective of Greg Sestero (Dave Franco), the struggling actor who Wiseau took under his wing to join him on his quixotic project. What’s great about the elder Franco’s performance is that it captures Wiseau’s eccentricities in a way that manages to playfully roast him and honour his misguided confidence at the same time.
It’s a portrayal so lovingly executed, in fact, that it wasn’t at all surprising to see Wiseau join Franco on stage when he won a Best Actor Award at the Golden Globes. That the show’s producers hit the music before Wiseau had a chance to talk was an enormous missed opportunity.
5. Faye Dunaway as Joan Crawford
A long time ago there was a movie called Mommie Dearest, a psychological horror movie that was actually (and quite indelicately) based on real events. For this one, the New Hollywood icon Faye Dunaway starred as the Golden Era icon Joan Crawford in a movie based on Crawford’s adoptive daughter Christina’s autobiography — which was, let’s say, a little uncomplimentary about her late matriarch.
This one goes into our list for pure camp factor and lore alone. In fact, Dunaway played the Mildred Pierce star with such insane energy that the movie’s distributors, Paramount Pictures, decided to market it as a dark comedy instead — despite the fact that it was depicting the real life physical and psychological abuse that Christina alleged in her memoir.
Whether or not that part of the story was true — the book was released a year after Crawford died and was refuted immediately and vehemently by her two other daughters — the performance has outlived the controversy and negative reviews (it was the second ever to be nominated at the Razzies) and is now beloved as a camp cult classic.
4. Margot Robbie as Sharon Tate
In Once Upon a Time… in Hollywood, Margot Robbie’s performance as Sharon Tate gives the movie its heart and soul. The focuses of Quentin Tarantino’s ninth movie as director are of course the misadventures of Rick Dalton (a down on his luck Western star, played by Leo DiCaprio) and Cliff Booth (his compellingly shady stunt double and bodyguard, played by Brad Pitt), yet the arc of the movie is less concerned about whether Rick will enjoy a comeback than if Tate (who was pregnant at the time with Roman Polanski’s baby) will survive an infamous night in 1969.
The then up-and-coming actress was murdered on August 9th of that year by the Manson family — a night that Tarantino gleefully recreates in his deliriously revisionist way, but Robbie doesn’t feature in that section of the movie. Instead, we get to see her dance in her bedroom, hang out with friends, and duck into a screening of The Wrecking Crew — the 1968 movie in which she appeared alongside Dean Martin. Tate’s career was too short for any of us to really have a strong idea of her, but there’s something in the way that Robbie performs in that scene, with her big goofy glasses on, that you sense Tate would have liked — Tarantino feet shot notwithstanding. A lovely tribute all the same.
3. Anthony Ippolito as Sylvester Stallone
To be clear: we are not saying that Peter Farrelly’s perfectly enjoyable I Play Rocky, the story of how Sylvester Stallone got that movie made, is anywhere near Once Upon a Time… in Hollywood in terms of quality. What we are saying is that Anthony Ippolito embodies the man so convincingly that even his impersonation of the iconic Stallone patter becomes quite endearing and lived-in after a while.
Granted, there isn’t a huge amount of competition for this title, but having convincingly done a young Pacino in The Offer — a 2022 miniseries about the making of The Godfather — Ippolito can claim to have done more of this kind of thing on a high level this decade than anyone else. Nominations will follow.
2. Cate Blanchett as Katharine Hepburn
Similar in some way to Stallone, Katharine Hepburn’s quick-paced and often quite haughty delivery is so well known to classic movie fans that the most challenging part of playing her is getting the voice down and getting past it to embody the role. In Martin Scorsese’s The Aviator, a flawed but compelling biopic on the business titan, Hollywood mogul, and increasingly kooky inventor Howard Hughes, the Bringing Up Baby star is played by the great Cate Blanchett — an actress who has probably never given a bad performance in her life, and she certainly wasn’t starting here.
No surprise, Blanchett nailed the clipped, mid-Atlantic accent without letting it overtake the whole performance. She also simply gobbles up all 25 minutes of her screen time, often overshadowing DiCaprio whenever the two of them share a scene. I would wager zero people in the audience at the 2005 Oscars were in any way convinced when she said in her acceptance speech: “When you play someone as terrifyingly well known as Katharine Hepburn, it’s a collaborative effort. You need as much help as you can get.” Yeah right.
1. Ana De Armas as Marilyn Monroe
Ana De Armas didn’t get to give an Oscar speech for playing Marilyn Monroe in Andrew Dominik’s Blonde: Michelle Yeoh won that year for Everything Everywhere All At Once, robbing Blanchett of a third win for her indomitable performance in TÁR — which made Yeoh the lucky benefactor of two movies that were probably a bit too hot at the time for the Academy to handle.
In the case of Blonde, a gorgeously constructed but bafflingly misjudged biopic of the most famous actress who’s ever lived, the voters were probably in the right. But you have to imagine, had the movie been just a touch more palatable, De Armas would have walked away with the prize.
Her turn as the former Mrs. Joe DiMaggio, Mrs. Arthur Miller, and star of The Misfits, The Asphalt Jungle and Some Like it Hot is simply phenomenal — both technically and emotionally. Surely no actor has been portrayed more often on-screen (Michelle Williams was also nominated for My Week with Marilyn) but De Armas managed to locate shades of her we hadn’t seen before; and for all the movie's flaws, the recreations of Monroe's most famous scenes and photographs are consistently immaculate. So much so that most actors would have gotten lost in them, but De Armas's Monroe still feels human and knowable. No mean feat.
