1999: The Podcast

EDtv opened in third place on March 26th right behind our last movie, Analyze This in 2nd and Forces of Nature in 1st, going on to gross $35 million worldwide on a budget of $80 million.

Directed by Ron Howard, it is a remake of the 1994 Quebecois film Louis 19, King of the Airwaves, with a script adapted by Lowell Ganz and Babaloo Mandel, it stars Matthew McConaughey, Jenna Elfman, Woody Harrelson, Ellen DeGeneres, Sally Kirkland, a frankly Oscar-worthy Martin Landau, Rob Reiner, Dennis Hopper, Elizabeth Hurley, Harry Shearer, Ian Gomez, Rupaul, Michael Moore, Jay Leno, George Plimpton, and Bill Maher.

EDtv tells the story of a regular guy whose life becomes a 24-hour reality show. It did modestly well with critics, but it was drowned out by 1998's similarly-premised (but in no way similar) The Truman Show.

Anyway, since it's the only 1999 movie to feature Bill Maher, we invited the host of the I Hate Bill Maher Podcast, comedian Will Weldon, to talk about this incredibly confused, frustrating movie, which remains notable for being the start of the McConaughey-Harrelson (possibly literal) Bromance!

Will's on Bluesky and other social media @oldmanweldon

57th on the 1999 box office chart, For Love of the Game marked director Raimi’s first foray into big-budget, mass-market filmmaking (which would ultimately pave the way for being handed the enormous task of finally bringing Spiderman to the screen in 2002)

But love and baseball was very different territory for Raimi, and his inexperience in the realm of pop movie making (as well as in directing romance) proved to be a hindrance.

For Love of the Game is, unofficially, the third and final entry in Kevin Costner's baseball trilogy, following 1989's Field of Dreams and 1988's Bull Durham.

The film tries to balance its dual nature as a romance and a straight sports movie, and while it occasionally hits the mark, most critics agreed: For Love of the Game is pretty great when it's about the game, and not so great when it's about the love.

But it's baseball season, and this was by far 1999's biggest baseball-themed movie, so we asked friend of the show - and White Sox diehard - Jacki Krestel to help us call some balls and strikes on this one!

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.