It's Oscars Weekend!

1999 was a weird year in Oscar history, as the awards held that year saw one of the most controversial Best Picture wins ever (SHAKESPEARE IN LOVE) and the awards held the following year honoring the awards of 1999 gave the Best Picture Oscar to a film that, well, has not aged well at all (AMERICAN BEAUTY)

So to mark the weekend, we took some time to discuss those two films and their legacies and discussed our picks for some of the worst Best Picture wins in recent history. We talk FORREST GUMP, BRAVEHEART, ANORA, CRASH, and more!

Analyze This was the 18th-highest grossing movie of 1999, opening on at #1 March 5th – the same day as Cruel Intentions, which opened number 2 - and taking in $177 million worldwide on an $80 million budget.

Analyze This gave us the unlikely comedy duo of Billy Crystal and (a then new to comedy) Robert DeNiro, alongside Lisa Kudrow, Chazz Palminteri, and Joe Viterelli

Directed by the late great Harold Ramis and written by Ramis, Peter Tolan, and, somewhat shockingly, Kenneth Lonergan, Analyze This made a lot of its then very novel premise of a gangster getting therapy...but also happened to be released a few months after the premiere of the The Sopranos.

This week, we're rejoined by our friend, comedy writer Chase Mitchell.

Chase is on the socials at @ChaseMit

It's Valentine's Day, so we're taking one last look at the non-1999 landscape before we return to 1999 next week with the movie that reset the standard for romantic comedies, Rob Reiner's When Harry Met Sally.

Joining us is returning friend of the pod Dan Colón, co-host of our podcast network's very own The Monsters that Made Us.

We talk Crystal, Ryan, Carrie Fisher, Barry Sonnenfeld, and if we've really seen a romantic comedy since (not called Notting Hill) that has come close to reaching its considerable romcom heights.

This week, Julia reports back from the screening she attended of "Father Mother Sister Brother", the latest from "Ghost Dog" writer/director Jim Jarmusch.

"Father Mother Sister Brother" is an anthology dramedy starring Tom Waits, Adam Driver, Mayim Bialik, Charlotte Rampling, Cate Blanchett, Vicky Krieps, Sarah Greene, Indya Moore, and Luka Sabbat.

Julia and John discuss the film and take another stab at what makes a Jarmusch film a Jarmusch film, the career of Tom Waits, great casting, and some of their favorite anthology films.

In honor of the late Rob Reiner we are looking at The Story of Us, the 74th highest-grossing movie of the year, finishing just ahead of earlier entry Blast from the Past. Opening #2 behind Fight Club on October 15th and going on to gross $59 million worldwide on a $50 million dollar budget.

Starring Bruce Willis, Michelle Pfeiffer, Reiner himself, Rita Wilson, Julie Hagerty, Paul Reiser, and Tim Matheson, The Story of Us is one of Reiner’s worst-reviewed movies, who, after an unbelievable run of movies in the late 80s and early 90s started running into trouble in the late 90s and early 2000s with the likes of this, Rumor Has It, and the aggressively sentimental and fluffy The Bucket List.

Is The Story of Us as bad as critics said? Or does it belong alongside When Harry Met Sally, Reiner's romcom masterpiece that it goes so far out its way to evoke?

We welcome Slate's Nitish Pahwa to discuss marriage, casting, bad writing, unnecessary monologues, and the greatness of Rob Reiner.

Nitish is on Bluesky @nitishpahwa.com

Merry Christmas and happy every other holiday!

In this episode, John and Julia each recommend five of their favorite "alternative" Christmas movies. The like of It's a Wonderful Life, Home Alone, Love Actually, Miracle on 34th Street, and, yes, even Die Hard are off-limits.

Instead, we present 10 movies that are maybe not in your annual Christmas rotation but ought to be! Enjoy!

Julia's picks:

The Ref (1994)

Carol (2015)

The Man Who Came to Dinner (1941)

A Christmas Tale (2008)

The Shop Around the Corner (1940)

John's picks:

Rare Exports (2010)

A Midwinter's Tale (1995)

8-Bit Christmas (2021)

About A Boy (2002)

Little Women (1994)

It's Christmas time, so we're looking at a movie that tells the story of a mysterious man who spends a lot of time on the roof with his animal friends and has the ability to sneak into your house undetected as if by magic: Ghost Dog: The Way of the Samurai!

Ghost Dog appears nowhere on the 1999 box office charts because it technically didn’t have a major theatrical release in the US until March of 2000 (it did begin its festival run in 1999, starting in May at the Cannes Film Festival where it was nominated for the Palme D’or)

Starring Forest Whitaker and written and directed by Jim Jarmusch with a score by Wu-Tang Clan’s RZA, Ghost Dog is a movie unlike any other, aggressively defying genre and staying laser-focused on its bizarre but endearing vision.

This week, John and Julia are joined by returning guest Sean Malin, author of the just-released book The Podcast Pantheon to talk Whitaker, Jarmusch, podcasts, Jon Hamm, and Christmas movies!

The first of what will be a series of smaller episodes where we take a look at a movie that is somehow related to our most recent subject.

This time, our See Also recommendation for The Insider is Billy Ray's superb 2003 docudrama/thriller Shattered Glass.

Featuring incredible performances from a uniformly excellent cast, especially Hayden Christensen as the title character and Peter Sarsgaard as New Republic editor Chuck Lane, Shattered Glass deserves it place among the best movies about journalism and the best movies of 2003.

It's also newly relevant in the midst of the Olivia Nuzzi of it all, and we talk about how the cult of personality around "The Writer" has impacted journalism for the worse.

You can watch Shattered Glass right now for free on Tubi.

Michael Mann's The Insider is easily the most glaring omission from the our initial 18, universally regarded as one of the best – if not THE best – movie of 1999.

Finishing in 69th place, sandwiched between two previous entries, Girl Interrupted at 70th and Mystery Men at 68th, The Insider stars Russell Crowe, in an Oscar-nominated performance, and Al Pacino alongside an incredibly deep supporting class (including the greatest character actor alive, Stephen Tobolowsky)

Directed by Michael Mann and adapted from the 1996 Vanity Fair article "The Man Who Knew Too Much" by Marie Brenner, The Insider received rave reviews, wound up on countless year-end top 10 lists, and was nominated for a slew of Oscars, including Mann for directing and screenwriting, but was shut out by the juggernaut that was American Beauty.

Since it's widely regarded as one of Mann's best films and one the best films ever made about journalism, we invited investigative journalist Lindsay Beyerstein to tell us how well the movie mirrors real life and to dig into what it's like to watch a movie about CBS News struggling to maintain its integrity as a journalistic entity in the bleak future of 26 years later.

Lindsay is on Bluesky @beyerstein

True Crime was the 94th-highest grossing movie of 1999, grossing just $17 million on a $50 million budget with a fairly limited release.

Starring and directed by Clint Eastwood, True Crime was largely forgotten and remains overlooked most likely due to its release at what can be described as Eastwood’s most prolonged artistic lull in the mid 1990s, starting with 1997’s Absolute Power and Midnight in the Garden of Eden, 2000’s Space Cowboys, and 2002’s Blood Work. That lull would end with 2003’s acclaimed Mystic River, which earned Oscars for both Sean Penn and Tim Robbins as well as Best Director and Best Picture nominations for Eastwood.

But True Crime is still an interesting entry on Eastwood's resume, exploring many of the themes of injustice and moral ambiguity that he frequently explores in his work. So does the similarly-themed 2024 film Juror #2, which Eastwood directed in his mid-90s.

So this week we're talking about them both, and joining is us is Aaron from the podcast Hit Factory.