Austin Powers: The Spy Who Shagged Me was the 4th-highest grossing movie of 1999, behind Toy Story 2, The Sixth Sense, and The Phantom Menace, opening on June 11 and taking in $55 million that weekend, going on to make $206 million at the domestic box office on a $33 million budget. Directed by Jay Roach and written by Mike Myers and Michael McCullers, The Spy Who Shagged Me saw Heather Graham stepping in to the Powers Girl role, replacing Elizabeth Hurley. The hugely anticipated and hyped sequel to the 1997 original, the movie came in with sky high expectations. The results were, well...mixed. But there's no question that Austin Powers was a huge cultural milestone, so we wanted to see how it held up. Helping us get the summer off to the most shagadelic start possible is actor, writer, podcaster, and activist ⁠Siri Dahl!⁠

VARSITY BLUES director Brian Robbins follow-up was another inspirational, somewhat edgy sports movie HARDBALL - this time about baseball and set in Chicago. 1999 icon Keanu Reeves plays down-on-his-luck sports gambler Conor O'Neill who finds himself the head coach of an inner-city Chicago youth baseball team. Somehow, he makes the team better. Somehow, the team makes him better. Diane Lane is also involved for unclear reasons. Is HARDBALL a good baseball movie? No. But is it a good movie? Also no. But the kids are great, including a very young Michael B. Jordan. Anyway, since it's about baseball and set in Chicago, Jacki Krestel is once again with us to talk about how, if you're going to make a baseball movie, you gotta actually demonstrate that you love baseball!

We sadly lost 1990s icon James Van Der Beek in February, so we decided it was time to look at his most prominent non-Dawson's Creek role - the teen comedy-drama sports movie Varsity Blues. Released very early in the year on January 15th, Varsity Blues was the 45th highest grossing movie of the year. Opening as a surprise number, it made back most of its 16 million dollar budget in its debut weekend and would go on to gross an impressive 54 million dollars worldwide, but it really became a summertime hit in its home video release in June. Also starring Jon Voight, Paul Walker, Ron Lester, Scott Caan, Amy Smart, Ali Larter, and a little baby Jesse Plemons, and featuring an incredibly 1999 soundtrack including Foo Fighters, Green Day, Collective Soul, Third Eye Blind and Fastball, Varsity Blues has something of a cult status, in part due to one very memorable line delivery. But how does it hold up as a teen movie or a sports film? This week, our friend Jacki Krestel joins us to talk sports, teens, 90s tropes, and James Van Der Beek. Jack writes about baseball on her blog, Jack Likes Baseball.

Last time we looked at Paul Thomas Anderson's 1999 film Magnolia, so we decided to take a look at his follow-up, 2002's Adam Sandler-led absurdist romantic dramedy Punch-Drunk Love. Anderson's shortest and most overlooked film, Punch-Drunk Love is now considered by many to be among his best. At 95 minutes, the film never faulters and drags, and its balance of performance, direction, and musical score amount to so much more than the sum of their parts. It also has some interesting connection to 1999, not least because Anderson - a huge Adam Sandler fan - was determined to cast him in his film after seeing 1999's Big Daddy.

We last talked about Paul Thomas Anderson's Magnolia nearly four years ago, so given Anderson recently (finally) won an Oscar for One Battle After Another, what better time than now for a revisit? Magnolia was a modest commercial success at the time but was lauded by critics, became something of a cult hit, and eventually worked its way into the cultural zeitgeist, in no so small part due to Tom Cruise's character Frank TJ Mackey (and his, uh...speeches). The film has, for a number of reasons, taken on new cultural significance in the ensuing years, and as Anderson's oeuvre grows ever larger, we wanted to know how and where Magnolia fits. Joining us this time is Holly Brown, Magnolia super fan and host/creator of the new podcast Everybody Knows But Me You can find out more about Holly at her website: https://www.hollyanabelbrown.com/

A president faking a war to distract from a political scandal?? WHAT??? We’re doing a new See Also this week, related to some of the recent movies we’ve discussed. The 57th highest-grossing movie of 1997 and the 46th highest-grossing of 1998. Released limited on Christmas Day 1997 and wide on January 4th 1998 where it finished 4th behind Titanic, Good Will Hunting, and As Good As It Gets, it went on to gross 64 million dollars on a 15 million dollar budget Directed by Baltimore Barry Levinson and written by Hilary Henkin and David Mamet, and starring Robert De Niro, Dustin Hoffman, Anne Heche, Denis Leary, Woody Harrelson, Willie Nelson, Kirsten Dunst, Andrea Martin, John Michael Higgins, Suzanne Cryer, Hollywood’s most famous Albanian Jim Belushi, and William H. Macy, Wag the Dog found itself on several year-end Best Of lists. It is certified fresh on RT with a score of 86 and a strong Metacritic score of 74. It was nominated for 2 Golden Globes – Best Picture Comedy, Best Actor Hoffman, and Best Adapted Screenplay for Henkin and Mamet, along with 2 Oscars -one, for Hoffman and the other for screenplay. Does it hold up? Spoiler alert: Yes.

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