The Wall Street Movies and TV Shows Worth Watching

Welcome back everyone.

Every year, I’ve run a “march madness” style tourney on my story where followers get to vote for their favorite Wall Street movie. Last year, the winner was The Big Short with The Wolf of Wall Street in 2nd place. In 2020, it was vice versa and we’ll have to see what the 2022 tourney has in store. 16 movies compete for the crown BUT not all these movies are actually good…so let’s go through my honest takes on each wall street movie and TV show. I LOVE watching finance movies and TV shows and often reference them through multi-layer jokes in memes. Here’s my favorite Wall Street movies:

Movies:

1) Margin Call: This 2011 movie is a semi-controversial choice though. Many people love it and say it’s their #1, while some critics say “I keep falling asleep”....Wahhhhh Boo Who. Ultimately, Margin Call is the most realistic finance movie IMO. Matt Levine also said the other day that Margin Call was his favorite finance movie, and simultaneously threw shade at The Wolf of Wall Street. This tense film takes place over 24 hours amid the early stages of the great financial crisis. The fictional investment bank in the movie slowly discovers things aren’t looking so rosy and needs to figure out what they can do to stay afloat. The ensemble cast is led by heavyweights such as Paul Bettany, Kevin Spacey (before we all realized he’s a huge PoS), Jeremy Irons, and Stanley Tucci. Irons’ performance as CEO John Tuld was my favorite, as he truly nailed the attitude and presence of a 2008 Wall Street CEO. The casting is great, the characters all have their own memorable quirks, and the delivery of lines is iconic. Highly recommend – especially if you want to understand the layers to some of the memes I put out there.

2) American Psycho: Out of nowhere this became my 2nd favorite Wall Street movie this year. I really started to love the satire in this movie and the absurdity of so many of the quotes (Ex: “I have to return some videotapes”). I think part of my newfound appreciation for this movie is from the sigma Patrick Bateman memes that started circulating Instagram this year.

Set in the 1980s, this 2000 movie stars Christian Bale as Patrick Bateman, a 27-year-old Investment Banker who is a serial killer by night. So ya, naturally the movie is pretty dark but is also written to be highly satirical. This horror/thriller/comedy is filled with quirky actors such as Willem Dafoe, who plays a detective, and Jared Leto, who plays the famous Paul Allen. It’s a fascinating albeit controversial movie, but most importantly for me, it's a source of an endless number of quotes and references.

3) The Big Short: Last year’s winner via the HYH Wall Street Movie Tourney. This 2015 film focuses on “four outsiders” who saw the housing market bubble in 2007 that no one else saw and bet against it. This ensemble cast is led by Christian Bale (Again) who plays Dr. Michael Burry (the guy that tweets weird stuff a lot and then quickly deletes his tweets), Ryan Gosling, Steve Carrell, and Brad Pitt. (Side note, my profile pic is Brad Pitt from this movie wearing a mask in an airport. A lot of ppl seem to think it’s a photo of me wearing a mask and ask me to take my mask off, but unfortunately, I can’t ☹. Sad!) This movie has a ton of other great actors in it – including Jeremy Strong (Kendall Roy in Succession) and brief cameos from Margot Robbie, Anthony Bourdain, and Selena Gomez in non-sequiturs to explain complex financial terms to viewers. This is a really fun ride of a movie.

My issue with the movie is sometimes it dumbs topics down to cater to a non-finance audience and the ending is a little weird. Some of the characters have a sense of “moral clarity” near the end which is a little uncharacteristic of the typical cynical short seller. Even with the dumbing down of topics for non-finance folks, this is still a hell of a movie.

4) Wall Street: Blue Horseshoe LOVES Anacott Steel. One of the OG wall street movies (released in 1987) with a young Charlie Sheen (Bud Fox) and Michael Douglas (Gordon Gekko) in his prime is one of the most entertaining wall street movies out there. Charlie Sheen’s character is willing to do anything to become a big shot and the legendary, but highly unethical, Gordon Gekko takes him under his wing to do his bidding. This movie is a must watch.

5) The Wolf of Wall Street: Leonardo DiCaprio and Jonah Hill balled out in this Martin Scorsese directed black comedy crime movie. Most people have seen DiCaprio’s performance as stock trader Jordan Belfort and many grew to admire the craziness and lavishness of Belfort’s life. This was also Margot Robbie’s breakout role and every high school/college guy was in love with her after this movie.

Personally, this one is only #5 for me as it’s a little too mainstream for me. The movie was more so debauchery focused than zoned in on more nuanced drama like many of the other wall street movies. Obviously, it’s still a great movie though as most of what Scorsese touches is gold (The Departed is one of my favorite movies – Scorsese also directed Taxi Driver, Goodfellas, Casino, Gangs of New York, and most recently, The Irishman). This movie is 3 hours long, but a hell of a story. 

I feel like at a minimum these first five movies I mentioned are must watch movies. Here are my reviews on the other big ones:

Barbarians at the Gate: I loved this one. The book of course is great, and the HBO movie does a really fun job bouncing around between all the craziness of the battle for RJR Nabisco between KKR and the management buyout team.

Too Big to Fail: This HBO TV movie stars William Hurt (R.I.P.) as Treasury Secretary Hank Paulson and Paul Giamatti as Ben Bernanke in their pursuit to save the financial system as the big banks started collapsing. This one is pretty entertaining with good acting across the board.

Boiler Room: Haven’t seen this pump & dump stock movie in a minute, but it’s solid. This might deserve to be higher, a lot of people LOVE this one – I just haven’t seen this in a while.

Trading Places: I thought this one was okay, but other people love it, so apologies for the disrespect in having this so low. It’s probably more of a generational thing where I only need to see this 1983 movie once. However, among many finance folk this is one of their favorite wall street movies. Eddie Murphy and Dan Aykroyd star in this film about a wealthy commodities trader and a street beggar trading places and the absurdity that unfolds as a result.

Rogue Trader: Ewan McGregor stars as young trader Nick Leeson in this underrated ride. Throughout the movie, Leeson accidentally loses a ton of money on a trade and covers it up instead of coming clean. Won't spoil what happens as a result...

Documentaries:

 Enron: The Smartest Guys in the Room – is a great documentary on all the tomfoolery that went down at Enron.

 Inside Job: This doc covers the buildup that drove the great financial crisis, as well as the initial fallout.

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Other Finance Movies:

Other People’s Money: Danny Devito stars as a corporate raider in this goodie but oldie. This one was actually an underrated, pretty solid movie, but not a top tier one.

The Wizard of Lies: Starring Robert De Niro as the legendary Bernie Madoff himself, this HBO TV film tells the story of the largest financial fraud in U.S. history. This was a pretty standard HBO movie, but I have no urge to rewatch.

The sequel, to Wall Street - Wall Street: Money Never Sleeps, was horrific, not even Shia LaBeouf at his prime or a younger Josh Brolin could save this movie. Garbage sauce.

Equity: A female led Investment Banking movie starring Anna Gunn (Skylar from Breaking Bad). Not a very good movie unfortunately, but it could’ve been okay.

Money Monster: This one was pretty bad. George Clooney stars as a parody of Jim Cramer that quickly becomes a tense affair when a viewer who went all in on a stock pumped on the show appears strapped to a bomb and holds Clooney’s Cramer hostage on live TV. Given how much Cramer gets mocked nowadays, I’m almost shocked no one references this movie, but that’s because it’s such a bad movie.

TV Shows:

Okay, time to dive into the TV Show segment and let y’all know where I stand on the big “wall street” shows, although I use the term loosely here given some of these are just business focused.

Succession: I meme this show constantly – because it is F-ing legit. It is incredibly well cast and perfectly tells a King Lear style story for a Media titan trying to figure out which child of his will succeed him as King/Queen of his massive empire. The constant backstabbing, political maneuvering, and back and forth jabbing coupled with witty and cruel banter make this show one hell of a watch (and rewatch, and maybe a third watch).

The recognition has been incredible – with the cast continually winning and getting nominated for awards. You can see Jeremy Strong, who won an Emmy and Golden Globe for his efforts, driving himself crazy in order to play the broken man that is Kendall Roy. In fact - Strong got so into his method acting for the role that everyone was genuinely concerned for his mental health. This shocking profile by The New Yorker highlights the lengths Strong put himself through to play Kendall. The Patriarch of the family, Logan, and his other children Roman and Shiv are also incredibly well played characters.

Two “outsider” characters Tom and Greg have incredible chemistry and are among many people’s favorite characters. This year, Matthew Macfadyen (Tom) won the Emmy for Outstanding Supporting Actor in a Drama Series.

There was criticism early on in season 3, which I think was merited, but proved quickly wrong at the end of the season. Unfortunately, throughout most of season 3, Succession became content with not really advancing the plot and creating real conflict, resulting in people starting to get tired of the back and forth witty remarks that led the show to temporarily move sideways. This changed later on in season 3 following the introduction of Alexander Skarsgard as Succession's version of Elon Musk. Now the show is in a prime position when it returns in Spring 2023 to have an incredible season. I’m amped – but hope they don’t drag the show out too long. Most TV shows are at their best when they know when to end (think Breaking Bad and The Wire), so Succession will likely be a 5-6 season show max to truly tell a relevant story that isn't too dragged out.

Billions: I quit halfway through Season 5 – recommend quitting after Season 4.

Some people quit far before Season 4, but I found that season very entertaining. Seasons 1-4 of this hedge fund drama are worth watching in my opinion, with a lot of good storytelling and fun characters during that time.

Damian Lewis, Paul Giamatti, and Maggie Siff are all very strong leads, but beyond that, the show has a really good ensemble. There are several characters you’d recognize as character actors that also add a ton to the show’s back and forth. One of the vibes I got from watching the show at its peak was that the cast was genuinely having a fun time. That’s what certainly made the show enjoyable, but eventually the show got a little too goofy.

The writing and plot really fell off a cliff in season 5, but there were some cracks of the writing starting to weaken even in seasons 3 and 4. Unfortunately but understandably, a key cast member left at the end of Season 5 after the passing of their significant other. Weakening leading characters coupled with supporting characters that were starting to get annoying definitely drove a lot of viewers away during Season 3-Season 5. You really just don’t see this show memed about at all.

The show is now on to Season 7 – and tbh I could care less. Look at this rise and fall below! No episode of Season 6 had more than 350k people tuning in, just embarrassing stuff.

Industry: Season 1 was terrible – Season 2 had some sluggish moments but turned things around significantly and had some very good scenes.

To be frank - this show is at its best when it sticks to finance and skips all the typical HBO/Gen Z shit. Obviously, they need the typical HBO/Gen Z shit though to keep the non-finance peeps engaged (since it’s not like the entire finance industry would carry viewership of the show). Plus, hey I get it, a tv show about finance without some level of exaggeration would be kinda boring.

It’s tough for me to say “Skip Season 1, watch Season 2” but it’s the truth. I don’t want to subject you all to 10 hours of a show that didn’t find its footing in season 1. It really did turn around in Season 2 though. Myha’la Herrold who plays the main character, Harper Stern, has really stepped up and gives some solid performances. The introduction of Jay Duplass as the TV version of Bill Ackman also gave the show a much needed spark in Season 2. Together, Herrold and Duplass do a phenomenal job during some very tense trading scenes.

The show was recently renewed for a 3rd season, it took a while for HBO to decide to renew, but they decided to give the writers another opportunity to build on the momentum they created in late season 2. Someone DM-ed me saying “Man, I never would’ve guessed watching Season 1 that I’d actually be rooting for a Season 3” – and that sums it up perfectly. Glad these guys get their shot – hopefully they’re able to zone in on making the show more like Succession and less like Euphoria or Pretty Little Liars.

Appendix: “Business” shows I enjoyed, but not necessarily “Wall Street” shows:

Silicon Valley: Man I wish this show was still running during all the craziness in 2021. The team at Pied Piper was hilarious and the show did a great job mocking Silicon Valley venture capitalists and founders. The show spanned six seasons from 2014-2019 and was a fun ride the entire time. Well done all around. I should probably find more windows to use this show in more meme templates.

Nathan for You: The host, Nathan Fielder, graduated from Canada’s top business school with really good grades (IYKYK). This show isn’t for everyone though because the goal of this show is to make you as uncomfortable as possible. Nathan is tasked with helping small businesses drum up new business, but his ideas involve adding more trouble than it’s worth and working to make everyone as uncomfortable as possible. Tbh, Nathan was “gaslighting” before gaslighting was a thing. If you haven’t seen it – you have no idea what I’m talking about – so you need to see it to believe it.

Some of my top episodes: The Ghost Realtor, The Movement, The Souvenir Shop (Part 1), Dumb Starbucks

Mad Men: Definitely a “business” show – albeit more marketing/advertising executive focused, this show aired during AMC’s peak as a channel and won/was nominated for a ridiculous amount of awards. This period piece starring Jon Hamm as the legendary Don Draper takes place during the 1960s-1970s and focuses on the rise and fall of advertising execs based in Madison Ave. Great show from start to finish, think I’ve seen this full series twice.

Lastly, there’s been a bunch of mini-series out lately on Silicon Valley founders that crashed and burned. I watched two mini-series on WeWork and Theranos that were okay and probably worthwhile for everyone else obsessed with these types of stories.

The Dropout: This 2022 Hulu mini-series stars Amanda Seyfried as Elizabeth Holmes and Naveen Andrews (from Lost) as her lover and COO, Sunny Balwani. For anyone who read WSJ journalist John Carreyrou’s book “Bad Blood”, this was a nice visualization of the rise, fall, and disgracing of the infamous Theranos founder who was just sentenced to prison for 11+ years. The show was nominated for six primetime Emmy awards with Seyfried winning the Emmy for outstanding lead actress in a limited series.

WeCrashed: Personally, I liked The Dropout more than this 2022 Apple limited series. Jared Leto and Anne Hathaway star as Adam and Rebekah Neumann in the stunning rise and downfall of WeWork. I think this show misses the mark a bit by having one of those “this is the fault of capitalism” style endings + spending too much on the rise up vs. the downfall (a lot of us remember in 2019 how crazy that was). It’s still worth a watch if you have the time, but not going to say that you’ll love the show.

Note* - I did not see Super Pumped, the Showtime show about the founder of Uber, Travis Kalanick. Some of the reviews online are okay, but I’ve heard from some people that they didn’t like it and the showrunners didn’t consult Travis at all during the making of it. So idk regarding that one.

That’s all for this edition! Until next time!

Btw – any ideas for the next newsletter or something to dig into in the future? Shoot me a DM, I’m open to ideas.