By Darren Franich and Keith Staskiewicz
Updated September 17, 2010 at 07:00 PM EDT

Sure, he was dating Madonna, but Warren Beatty’s life wasn’t perfect. The year was 1990. Beatty was coming off of Ishtar, a mega-flop and a rare misstep in a glorious career. The famous ladies’ man was still the portrait of Hollywood glamour — again, dating Madonna — but before Ishtar, he hadn’t made a film since 1981’s epic Reds. He turned to a curious labor of love: an adaptation of Dick Tracy, a 60-year-old comic strip about a lantern-jawed detective who fights magnificently ugly criminals. The timing was perfect: Tim Burton’s Batman came out the year before Tracy, and set a gold standard for comic book adaptations, merchandising, blockbuster promotion, and generally making a boatload of money off of comic-based movie with a tweaked approach to set design. Lest you doubt the connection, the two movies share a nearly identical Danny Elfman score. (Seriously, the dude just Xeroxed his Batman sheet music and made a couple changes.) With all this in mind, and in honor of this week’s release of two other movies directed by actors (Ben Affleck’s The Town and Philip Seymour Hoffman’s Jack Goes Boating), we discuss that crime-busting, yellow-coated man with the two-way radio watch, Dick Tracy.

Darren Franich: This might be the most Oscar-heavy cast ever assembled for a comic film. There’s Warren Beatty, Al Pacino, Dustin Hoffman, and Kathy Bates as a stenographer. The film’s shot by Vittorio Storaro, who won Oscars for Apocalypse Now, Reds, and The Last Emperor. Throw in Dick Van Dyke, Madonna, and the original songs by Stephen Sondheim, and Dick Tracy officially has a team EGOT.

Keith Staskiewicz: And for the first time, Al Pacino really plays an outsize caricature of himself, which he then carried with him throughout the following 20 years. All of the mannerisms are there: sudden outbursts, table slapping, a permanent scowl. It’s like he’s wearing a Halloween mask of himself, which ended up melding to his face and becoming the real Al Pacino.

DF: Just like in Goosebumps! Weirdly, I think Pacino’s really good in the movie. Especially in the last few minutes when he starts free-associating. “Does life imitate art? Can’t you see that I love you?” Actually, everybody’s good in the movie except for Warren Beatty.

KS: He’s too old for role, and barely emotes.

DF: He tries to play Tracy as the square-jawed cartoon guy, but also as a more emotionally realistic character. When in doubt, he just looks confused. In all the Madonna scenes, he looks like a flustered middle-aged man getting tempted by a showgirl. It’s like a color-saturated re-enactment of The Blue Angel.

KS: Dick Tracy reminds me a lot of Speed Racer. Neither is a great movie, but both are unique in how they approach their story visually. Racer is all about color and motion and futzing with the notion of montage to make it feel less like a movie and more like a live action cartoon. Tracy exists in this candy-colored world that’s totally fake-looking: backlots that look like backlots, only seven colors, matte paintings everywhere. It’s almost avant-garde in how it tries to resemble a four-color comic strip.

DF: Beatty was trying to imitate the Sunday-comics feel, but the original was a really gritty strip, full of blood and really amoral characters. It’s still pretty disturbing today. To me, Dick Tracy is basically a premake of Sin City. Both are based on gritty metropolitan noir comics, both look utterly gorgeous frame-by-frame, both were made by directors fixated on translating the graphic-narrative feeling into movie form.

KS: And both fail in the same way: the characters are turned into cartoons along with everything else. It’s still fascinating to think that the same person who did Reds, which is by all means a pretty classically-shot movie (also by Vittorio Storaro), then turned around years later and produced this. So many talented people were so invested in a movie about a character from a 30-40-year-old comic strip that no moviegoers were really clamoring to see adapted. Which, again, makes it a lot like Speed Racer.

DF: That’s why Tracy feels like such a gem. It seems like a legitimate labor of love by very creative people, whereas even the best comic movies now feel like the director is telling the studio, “Okay, I’ll make this superhero movie, but then I want to make my surrealist dream thriller/Hitler-killing movie/whatever Drag Me to Hell is.”

KS:Beatty’s line is always that he never plans to direct anything (well, other than Reds), but that he ends up doing it because no one else is there. Of course, it’s also because he’s a control freak, and directs even when he’s not directing, but I don’t think he really expected to direct this coming off of Reds. But it ended up as a labor of love.

DF: He plays Dick Tracy, and someone literally says his name ten times every minute. “Tracy! Tracy! Dick Tracy! Tracy! Are you there, Tracy?” It adds a weird, hyper-narcissistic element to the film.

KS: Coming off of Ishtar, he’d suffered a huge blow. He hadn’t had that many flops before. He had turned 50. Could he still play a ladykiller? And if not, then what? So it kind of makes sense that he’s cast as this figure that everyone looks up to, like a movie star. But he’s also a movie star that takes action, that actually does stuff. Like, say, a movie star that also directs. Dick Tracy is essentially the tale of Warren Beatty. Madonna, the singing temptress, comes along to seduce Dick out of the possibility of a long-term relationship. But in the end, he chooses monogamy and the family unit over sexy divas and Stephen Sondheim tunes. Yay, Annette Bening!

DF: It’s an interesting subgenre of movie: Dick Tracy, Sin City, Speed Racer, and I think you can throw in Ang Lee’s Hulk and Bryan Singer’s Superman Returns. Like, “Movies based on established, even utterly-cheesy comic franchises, which directors who fancy themselves auteurs try to adapt religiously, but in attempting to perfectly translate the original material to the big screen, they instead create a navel-gazing auteurist self-portrait.” There must be a shorter way to say that.

KS: Let’s call it nostalgiauteurism. No wait, that sounds like a neurological disorder.

Next Week: Waiting for ‘Superman’ is a film about an education system that has lost the power to educate. Superman II is a film about a superhero who has lost the power to fly. Both are mandatory viewing next week.