Is 'Once Upon a Time ... in Hollywood' Leonardo DiCaprio's Best Performance? | The Rewatchables

Live from the Sundance Film Festival, The Ringer’s Bill Simmons and his stunt doubles Sean Fennessey, and Chris Ryan are a gang of has-beens trying to keep the magic alive in the Golden Age of Hollywood when they rewatch 2020 Best Picture nominee ‘Once Upon a Time … in Hollywood,’ starring Leonardo DiCaprio, Brad Pitt, and Margot Robbie, directed by Quentin Tarantino.
Subscribe to our channel: therin.gr/5te1wFL
CONNECT
Shop: theringer.com/shop
Website: theringer.com
Twitter: / ringer
Facebook: / ringer
Instagram: / ringer
KZbin: / @theringernba

[@ILikeKoreanGirls]

That Nowitzky getting a title parallel is perfect for Brad's performance here.

[@David-iv6je]

But Bill has never figured out how to pronounce his name. Damned Irishman.

[@tonybalsamo8673]

Eight god damn whiskey sours?? You couldn’t stop at three or four, you had to have EIGHT!!??

[@jordan12118]

That Hippie that had the monologue about "killing the people who taught us how to kill" won the Dion Waiters award for me. She was fantastic

[@enzorossi9853]

It's obvious Tarantino loved her overacting thats why that take stood in the movie lol

[@NikeSocks24]

They forgot about Tom Cruise as Frank TJ Mackey in Magnolia....deep performance

[@ambrosaur3646]

Also Tom Cruise as Vincent in Collateral. He has a great acting range

[@rufashaochicken]

these three is one golden trio

[@TonyDanza4Lyfe]

Nah Sean is garbage

[@NicolasEu]

hands down the most rewatchable film of 2019.

[@mutton7891]

That would be Parasite for me.

[@SN2903]

Joker

[@ambrosaur3646]

Alongside Uncut Gems and Parasite

[@jakegraham3758]

Signature Leo role of last 8 years? Wolf of Wall Street

[@IanJacobyandcompany]

I was screaming this at my laptop too. Thank you. Plus magnolia obvy about the tom cruise part. These guys were on one that night.

[@jakegraham3758]

Adam Price very true between that and the departed those are is two most unique roles by far but I just didn’t say Calvin because he wasn’t in enough of it but yeah that’s his best performance ever if I could give him a Oscar for just one it’d be Calvin candie

[@9009matorres]

I don’t even know if there’s a signature role...there’s just years of consistency. For me his best role is Hugh glass. Wolf is his most over the top performance and he def should’ve won that Oscar

[@ddubs0606]

Anyone else not really into wolf? Great performance but…

[@blakeharris58]

I’m going with Django Unchained.

[@bnns]

I liked that they roasted Bill's takes numerous times on this one, I love Bill, he just gets carried away sometimes and Sean and Chris were like: dude, what?

[@ColdColdColdGround]

love the way Sean and Chris play off each other in most of the ones they're both on together.

[@David-iv6je]

Simmons is great at pop culture in the same way he is great at basketball details, but some of his movie takes are downright awful.

[@fuiers]

I think the role what we remember Leo in 5 years time will be Wolf of Wall Street. There is so much rewatchable stuff in that one. It keeps up. Brad on the other hand is the one id concur. This was his best role in years.

[@august6389]

Matthew stole the Oscar from Leo

[@Garrett1240]

Wasn’t Pitt in the tree of life? His best imo.

[@lionheart4299]

@@Garrett1240 I guess you missed 12 monkeys!

[@Backfromthestorm]

The Basketball Diaries

[@rickyc1709]

How the hell does Julia Butters not win the Dion Waiters award?

[@jordan12118]

The Hippie with the "kill the people who taught us to kill" monologue should've won

[@djstarsign]

Because Simmons has zero taste.

[@phialpha88]

True

[@Telecasterluvr]

You could say this is Leo’s greatest performance for like 8 of his movies. That just shows how consistently amazing he’s been for the past 20 years. My personal favorite is The Aviator. Dude delved so deep into Howard Hughes

[@phillipprill8933]

Jake Lineman Agreed. I rewatched that and Catch Me If You Can for the first time since they were in theaters. I underestimated how great he was in both because he wasnt on my radar at the time to become “Leo”

[@0113Naruto]

Wolf of Wall Street has been his best performance.

[@ZR38315]

I don’t know if it’s my favorite but I think the aviator is his most underrated movie. It’s never talked about anymore but it’s fantastic and really doesn’t lose any steam over 3 hours. Plus Blanchett might be even better than Leo in it

[@coreygolphenee9633]

Hes the tim duncan of acting

[@morganwu767]

IMO Wolf1 Hollywood2 is pretty undisputed. You could probably say Django but it’s a supporting role

[@LoadedGunn47]

Wasn't sure what a Rewatchables would be like with a live audience but this was the most fun I've had watching one yet, it's clear you guys were having a great time

[@michaelserby7697]

Cliff's dog Brandy deserves an Oscar 🇺🇸 💙

[@Bluemgwes]

She won the Palm Dog award at Cannes!

[@donkydoodledoop369]

Cliffs footwear in that movie should get 4 Oscars eaaaasy

[@benjeezyyabeezy]

I've been saying this was the best Leo performance ever to all my friends and now I feel validated

[@Isaac-gf3jt]

Ocen upon a time was a absolute blast. Second best movie by Tarantino after Pulp, and top 10 all time favs of mine.

[@edtallman7264]

I totally agree. Good post.

[@BoutYoungAnnaLee]

Leo should’ve won the Oscar. He’s playing an actor, playing various roles, displaying every emotion dialled up to 12, plus he’s insecure as hell. I didn’t see a single performance that year to match it tbh

[@kyle1137]

Absolutely, he was completely underrated

[@JNovoa-cu4pv]

You’re probably right but Joaquin was overdue for an Oscar & Leo already had his

[@jacobaframian3182]

I along with Bill didn’t realize that was Lena Dunham either.

[@zacharybear2138]

My skin did.

[@jordan12118]

Neither did I.

[@MegaRudyray]

I left with like 3 new songs I dint know I liked. He does that every time.

[@zyrrhos]

The trailer freakout is in my opinion Leo's best performance ever.

[@ZR38315]

Bearded Jagger id prob still lean towards Django or Wolf of Wall Street but he is def great in this

[@zyrrhos]

@@ZR38315 Those are the other two in my mind as well. He plays big characters really well. Subtle real characters? Not so much.

[@MegaRudyray]

That is pretty awesome. I like when he says fuck it, and takes a drink, then immediately gets mad at himself.

[@roycema]

I go skull scene django

[@zyrrhos]

@@roycema That's a good'un. Although the trailer scene feels a little more grounded in reality to me. The skull scene is pure entertainment. Nothing wrong with that, but I see subtleties in the trailer scene that I just marvel at.

[@brewer921]

The best quote has to be: "Don't forget. You're Rick Fucking Dalton."

[@TheGodfather-bm3ow]

Cruise was in tropic thunder .. best bit part

[@kbob9625]

He’s insane if he doesn’t think the revenant want good. Leo was amazing in that movie.

[@tct8284]

Tom Cruise as a Star Fleet Captain in a Tarantino Original Star Trek script

[@andrewgundy3045]

Leo was absolutely hysterical in this

[@ENigma-um8zw]

Bill Simmons getting the Boogie Nights house and then doing that episode in that house with the crew is like his version of Gary Vaynerchuk talking about buying the NY Jets lol

[@MaximLight269]

Did you guys forget Leo's in Django?

[@TonyDanza4Lyfe]

Yeah he's awesome in that

[@meandave]

Everyone disappeared in the Bruce/Cliff fight right after Cliff throws Bruce into Zoe Bell's car, you can see reflections of them taking off like "Holy shit, that's boss lady's car", so it may not be so much some aspect of Cliff's reimagining as much as self-preserved response of the crew watching

[@somemale]

Yes. My take is that for sure it all happened like that and when looking back at it, Cliff realized he messed up and deserved to get fired. Him being able to take on Bruce Lee without any fear shows his character throughout the movie.

[@brad7932]

These goofballs missed it, cos they're the exact pussies that would run'n hide when shit like that happens. Must be a coping mechanism to seeing their own pussy behaviour represented on the big screen 🤣 Cliff is Tarantino's most dangerous character. An absolute killing machine.

[@justinb928]

I'm surprised that they haven't done a rewatchables for Vanilla Sky. The guys have good taste and that role for Cruise, is to me his best performance. Very underrated film and Cruise and Crowe are a good duo.

[@kamtheman106]

Justin Brown Fennessey and Ryan have good taste. Bill - very clearly - does not.

[@twpence]

best performance for me is magnolia by far

[@blakeharris58]

Great performance but the movie is not rewatchable.

[@votdfak]

Vanilla Sky vs original Abre Los Ojos... Vanilla Sky is trash...

[@mrebear9758]

​@@twpence100%

[@deangelovickers66633]

Best of the year. Best performances ever for Pitt and Leo.

[@keeganshigh]

Dumb.

[@tommyo.3535]

What an incredible Linda Partridge impression

[@TheWaynos73]

This is a pretty unique film in Tarantino’s career - where most of his films are dialogue and monologue driven, Once Upon a Time in Hollywood isn’t. Quentin actually shut his big mouth on this one and delivered more of an image and mood piece.

[@lilpenny1982]

Brad Pitt's best performance was in Legends of the Fall or Se7en

[@zyrrhos]

I think QT shut down the cancellers with his short eloquent response to that retweet seeker at Cannes.

[@mjm5081]

Exactly

[@gabrielsoyka5189]

link? id love to see this

[@blakeharris58]

He told a woman who insisted that Margot Robbie didn't have enough dialogue that he "disagreed with her premise".

[@zyrrhos]

@@blakeharris58 "Well I just reject your hypothesis." Link above.

[@blakeharris58]

@@zyrrhos ah ya got me. I was close.

[@CharlieHustle1687]

Really wish this wasn’t done in front of an audience, it’s not the same and this was an epic movie

[@johnmorris8444]

I disagree with the reading of the Bruce Lee part. The bystanders didn’t disappear. Once Bruce got thrown into the car the only guy on screen runs off and it seemed obvious that everyone scattered like cochroaches so they aren’t implicated once the boss shows up and sees her car destroyed. I didn’t read this as a dilution at all and upon rewatching I don’t see how you can.

[@MarcFritzer]

That definitely aged the worst

[@johnmorris8444]

@@MarcFritzer how so?

[@Paul-ew5st]

@@johnmorris8444 The guy doesn't run off he goes to the phone even more reason for everyone to scatter he calls Randy

[@jakecampbell3524]

I hope one of you reads this, but Tarantino came out and said that the Bruce lee fight scene absolutely did happen in his story and was not made up by cliff. Seemed like kind of a stretch/reach when you guys mentioned it so I had to look it up

[@floridagator1765]

Leo did a great job. So did Brad Pitt.

[@TonyDanza4Lyfe]

See this is why Bill is my dawg. I felt like I was the only one in the world who remembered Wiig n will doing that movie and he brings it up. The man

[@SLIDESPOT]

YES and YES.....first time I watched it Brad Pitts performance stood out more but then as i kept watching that film, over and over and over again I would laugh in amazement over what Decaprio was doing....he was the dude playing a dude disguised as another dude and that third act rant was so funny

[@MegaRudyray]

At one point he was a dude pretending to be a dude, watching his fake dude pretending to be a dude on tv. If that makes sense.

[@MrGMovieReviews]

The Wolf of Wall Street is his best performance. But Aviator and Hollywood he's also incredible in

[@natatatt]

I preferred Leo in The Departed in 2006 over "Once Upon a Time...".

[@stevemoneybags9484]

Nat T which character? The one with a Boston accent or the one without?

[@Serit0nin]

Can someone tell me which 3 podcasts they do with QT that they reference?

[@bkc6873]

World class performance by Sean

[@GeronFletcher]

Drive in movie theaters definitely still exist lol

[@brewer921]

"Brother Love's Travelling Salvation Show" is one of Neil Diamond's signature songs. Bill has some bad takes.

[@djstarsign]

brewer921 dude constantly displays high levels of ignorance with such confidence. It’s kind of embarrassing.

[@jackdriscoll8387]

here on november 16, 2021, and that elvis movies TRAILER just came out

[@davidkirkham1656]

The most rewatchable scene is easily the fight scene

[@ryanfrank4500]

Which of the two houses from Boogie Nights is Bill talking about buying? Jack's house or Alfred Molina's house?

[@cliffbooth8423]

I like the Slapshot mention. Paul Newman as coach/player Reg Dunlop is one of his best roles!

[@samanthab1923]

Jimmy Jammy Absolutely should have won for the Verdict! Robbed him so gave it to him for Color of Money

[@samanthab1923]

Still funny. The fashion show 😂

[@connoreasterday306]

I’m so fucking happy that this happened

[@rigsby1454]

Mad that the Drive In set is a model. I love QT

[@2160michael]

Why is Chris giving Sean shit about working out with Leo so damn funny?

[@brewer921]

Wolf of Wall Street and Focus were two years apart. Can I interest you in some Apple stock?

[@MichaelADAddario]

The Revenant isn't good? LMAO Good lord.

[@isuriadireja91]

to me...YES. his performances in Django Unchained and The Wolf of Wall Street tie in second place.

[@crg750]

We just need QT to show up on this and we've got a full blown case of epicness! The homey Chris Ryan is really getting some mileage out of that Penfield beanie... step up your game CR and diversify your shit! toss in a sick Supreme beanie or maybe even some Aimé Leon Dore! Level up!

[@winthorpetrois]

I don't understand why he wears that. Is he OK?

[@TheCoolhanddan83]

Love these vid companions now!

[@MarkMarxonsBassChannel]

Definitely up there with his best

[@THE_BEAR_JEW]

Brad's best for me will forever be in Snatch. He's a minor character but he was captivating in that role. Leo's is the Departed.

[@sianspherica]

1. Wolf of Wall Street 2. Once Upon a Time in Hollywood 3. The Aviator 4. The Revenant 5. The Departed

[@bobbowie9350]

Blood Diamond is no 1

[@roycedot]

Can't believe they are complimenting Brad's "acting" in this film. It's probably the least he's acted in his career. Like they said, he's now just a chill guy in real life. Cliff Booth is just 60s Rusty from Ocean's. Non-emotional, just going with the flow. Compare Cliff to 12 Monkeys, Snatch, Interview with the Vampire, Burn After Reading, Benjamin Button

[@davidpesekmuller3883]

Good point, he's awesome to watch but he's just George Clooneying his way through the film..

[@mjm5081]

If only it could've ended like that in real life...If only.

[@markporter7657]

Loved this but have one nitpick: the spectators don’t disappear as a plot device, they can be seen in other parts of the fight, and leaving near the end. They likely were there but leave because their boss shows up and they don’t want to get in trouble. I’m not saying Cliff’s recollection is all true and accurate, but it makes me believe the incident did happen in some form.

[@shitpostheavy]

I hate how inconsistent (and random) how the podcasts / videos are. Like which ones will have a visual component and which will be audio only? I'd 100% support the KZbin channel but it's a constant check for every podcast content.

[@bryancaulfield2066]

There needs to be some epic ensemble film with DiCaprio, Pitt, Bale, McConaughey and Phoenix. I'd go Fincher or Thomas Anderson as director.

[@blakeharris58]

It would need to be a horror/thriller. Fincher directing.

[@pabl0sauced0]

"Whats DiCaprio's most memorable role in the last few years. Blood diamond?" Has thus dude not been to a movie theater since 2006??.. 🤦😂

[@darshin95]

NO WAY. It's The Aviator hands-down

[@mjwbulich]

Just as an aside, you cannot smoke LSD. Cliff is either smoking DMT or more likely based on his demeanor PCP.

[@TheGodfather-bm3ow]

Yeah I remember Leo as jordan from wolf of wall street ... and Pitt as Achilles

[@michaelcummings8763]

50:39 what was the suggestion the audience member made? was it to swap them?

[@TheRleagle2012]

Michael Cummings pretty much if they switched the roles, if Leo played pitts character and vis versa

[@9009matorres]

Doesn’t work if they switched IMO. Brad has a more rugged look, definitely has the physique to be a stuntman. Leo (who I’m a huge fanboy of) is skinny fat. Plus still has a baby face. Not rugged enough.

[@MrGMovieReviews]

Sean you know damn well Johnny Depp shouldn't be cancelled.

[@michaelcummings8763]

MrGMovieReviews has there been a cancel reversal between Depp and Amber Heard? like UNO?

[@MrGMovieReviews]

@@michaelcummings8763 actually yes lol

[@jakegraham3758]

I feel like he’s immune to it every time something comes up about him he dips for a second then will pop out with another decent performance

[@MrGMovieReviews]

@@jakegraham3758 he was incredible in Black Mass

[@MarkAS56]

I'm gonna say Leo will do Bounty Law if Tarentino really gets the opportunity to do this.

[@lpr5269]

One of my favorite lines was Julia Butters as Trudy saying to Rick "I don't like names like pumpkin puss, but since you're upset, we'll talk about that some other time."

[@FoodJapan]

Damn Sean was throwing heat this episode. Was he drinking?

[@georgeparker8198]

I agree with Bill, Focus was amazing. It's crazy to me that no one else but me and Bill seem to like that movie 😂

[@andrewdeen1]

Damien Lewis was playing Michael Madsen

[@dmccoy9848]

Captions say Shawn Fantasy and I really think he should go with it

[@jaycepero8069]

The Aviator is Leo’s best performance.

[@loganbennett5418]

RDJ and Tom Cruise

[@brewer921]

There is a plot in Smokey and the Bandit. Bootlegging Coors across state lines.

[@cauecarneiro6545]

I'm sorry i didn't understand anything you guys said, i was fixated in Bill's inability to properly hold a mic

[@ashtokm]

I saw a Ringer piece with Bill and Joe House playing golf. If you had seen that, the mic technique would be no surprise

[@salvatoresultana4058]

The Nice Guys as Rick and Cliff

[@toppatop21]

I'm a huge Tarantino fan and i'm a fan of Brad Pitt and especially Leo and though they were good I disagree that these were their best roles. Leo was way better in The Departed, Blood Diamonds, Gilbert Grape, Wolf of Wall Street and Django........this movie cannot compare to True Romance, Pulp Fiction, Inglorious Bastards, the Kill Bills...they were all more entertaining than Once Upon a time ...

[@austinmarin9334]

I can't trust anyone who wears a beanie indoors

[@manny44]

as a fellow bald man....I get it. Not a matter of trustworthiness.

[@pvthitch]

Oy vey!

[@rachnakapoor2685]

Boogie Nights 30:00

[@15awesomehighfive]

Chris Ryan is simply the best.

[@wolfwilliams]

Of the three on here, he's by far the best one to go to for movie takes. Fennessey is unlistenable, and Bill's act is old now.

[@stardestroyer44]

Disagree. Ryan sucks.

[@jennycraigadventures3314]

Matt Damon and Mark Wahlberg both using they’re best South Philly personas...and have them switch roles in the middle and see if anyone notices.

[@marshallhealey858]

We have heard so much of Bill making Sean uncomfortable about sexual situations in movies and finally, at 58:39 we see what it looks like. I am not disappointed.

[@JNovoa-cu4pv]

57:24 Pulp Fiction, Training Day, Chinatown, The Big Lebowski, LA Confidential, & Menace II Society are also great LA movies

[@bobbowie9350]

LA story. Lalaland

[@ricky93100]

Guy sounds just like Sean Evans from Hot Ones

[@iwasgonnasay]

no chance this should win best picture over parasite

[@jennycraigadventures3314]

ejs 1. 1917 2. Parasite 3. Jojo

[@michaelb3927]

I HATE anyone older asking "do you even know what that is?" Lol I was born in the 80's but I've still heard every Beatles song. So, regardless of growing up in the 90's I'm very familiar with them, seen all Smokey and the Bandit movies even the god awful Jerry Reed "playing bandit " access to all media world wide BS 😉🤣 wasn't around for the Vietnam, but I've seen it in color and heard plenty of G.I's first and second hand accounts 👌 just a peeve for a history buff

[@frankmaitland2569]

Release the 20 HOUR CUT.

[@Lancaster51]

Bill Simmons thinks every movie should be 80 minutes or less

[@hammadasif3006]

The Wolf of Wall Street The Aviator Leo's top 2 performances still Can rank them one or the either

[@jakegraham3758]

Hammad Asif he’s pretty great in the departed...... basically he’s untouchable when working with Scorsese

[@chiara8561]

The Aviator followed by What's eating Gilbert Grape and Revolutionary Road (underrated)

[@scottbarkley496]

The disrespect to Tom Cruise is unreal. His last movie "Fallout" is his most successful best reviewed film in his 40 year old career & yet these dorks aren't giving him any respect.

[@niklaszillig7282]

It’s a MI movie that hardly qualifies as a masterpiece. Of course it’s going to be successful, it’s a major franchise.

[@tpjohn8]

@@niklaszillig7282 Yeah but it's a 'major franchise' because of him. Like there is no Kevin Feige pulling strings from behind, making all the creative decision. But the MI movies revolve around cruise. if these movies flopped every blame would be on Cruise so if they succeed every accolades should for Cruise as well. You can call it an IP its just that he IS the IP.

[@august6389]

I think you're confused. They weren't disrespecting Cruise. Listen again

[@gorkmusic]

Django and Wolf Of Wall Street are more iconic roles because the movies are just way more fun.

[@johnmorris8444]

Why are they so down on Cliff , that he’s a bad guy or a “shithead”? I’d classify him as a good guy. Has a job helping his friend and doesn’t complain once regardless of what is asked of him. Offers a ride to a hitchhiker and turns down her advances. Looks out for an old man being taken advantage of. Takes good care of his dog, kills a bunch of homicidal maniacs. Never loses his cool. Only thing against him is some gossip about his wife.

[@ZR38315]

I mean it does really seem like he killed his wife

[@johnmorris8444]

@@ZR38315 yea, probably did. Even in his own memories it looks like the case but it’s still heresay. Complicated character but I still consider him the good guy.

[@lpr5269]

@@ZR38315 In the book he accidentally pulled the trigger on the spear gun, and was really upset after and brought her to the hospital, but it was too late to save her.

[@lionheart4299]

Yes that’s Leo’s best and Tom cruise has had very iconic roles. His best was magnolia, born on the 4th was great, interview with the camp, few good men, guys great!