Originally Reviewed in June 1999 | Updated in December 2024
Ah, the late ’90s—a time when racing games were all about speed, chaos, and just a little disregard for the rules of the road. Enter Midtown Madness, the 1999 open-world racer from Angel Studios (before they became Rockstar San Diego, mind you) that delivered exactly what so many of us wanted: total driving freedom in a sprawling American city.
When I first picked up Midtown Madness, I was searching for a game that could capture the thrill and physics of Carmageddon but without the gory “run over pedestrians to win” mindset. I wanted something chaotic but grounded in pure racing adrenaline—stunt driving, reverse 180s, and white-knuckle 90-degree power slides that left your opponents eating your dust. Midtown Madness gave me that freedom and a brand-new treat I didn’t even realize I was craving: a real American city to explore—Chicago, complete with streets, traffic, and police. Sure, it stumbles in a few places compared to Carmageddon, but it also nails so many other elements that make it an essential ’90s classic.
Freedom, Chaos, and the City of Chicago
At the heart of Midtown Madness is its open-world interpretation of Chicago. Even today, there’s something charming about cruising through a simplified yet instantly recognizable Windy City. While it’s not perfect—generic buildings, no back alleys, and a few iconic landmarks placed for fun rather than accuracy—it still feels alive thanks to its traffic systems, pedestrians, and police presence. Little touches, like garbage cans flying down the street after a hard collision or traffic signals dictating civilian car behavior, give the city personality.
That said, Chicago does take some liberties. For example, bridges over the river are perpetually raised—an unrealistic choice that somehow makes the game more fun. Why complain about realism when it’s an excuse for some sweet mid-air jumps?
Game Modes: Something for Everyone
Midtown Madness comes packed with a solid variety of modes that still hold up:
- Cruise Mode: The perfect sandbox for driving enthusiasts who just want to let loose—run red lights, weave through traffic at breakneck speed, and honk obnoxiously at everyone in sight. Pure, unstructured chaos.
- Checkpoint Race: A freeform, strategic race where you plot your own route through a bustling city. Cutting through traffic, dodging pedestrians, and barely skimming past intersections makes each race feel thrilling and unpredictable.
- Timed Runs: The game’s version of a solo challenge—beat the clock as you speed from checkpoint to checkpoint.
- Circuit Races: A more traditional racing experience, where the city transforms into a closed-track environment for intense competition.
What Midtown Madness lacks in track variety, it makes up for with its AI opponents. The computer racers are aggressive, unpredictable, and genuinely challenging. My only gripe? You can’t tweak the difficulty level.
Multiplayer Mayhem
Even back in 1999, Midtown Madness knew how to keep friends entertained. Multiplayer modes included standard races and the standout Cops and Robbers mode. In this team-based game, players scramble to find a gold bar and race it back to their home base while opponents (often screaming through their dial-up connections) try to crash, smash, or intercept you.
Even with a 33.6k modem, Midtown Madness was surprisingly playable. Microsoft Gaming Zone hadn’t fully implemented DirectPlay at launch, but when it finally hit, the multiplayer experience became a highlight. This mode alone kept me (and many others) glued to our screens—shouting, laughing, and definitely not caring about realism.
Vehicles: From Beetles to Buses
The vehicle selection in Midtown Madness offers a delightful mix of styles and personalities. You start small—cruising around in a classic VW Beetle—and eventually unlock faster, heavier, and downright absurd vehicles like a Ford F-350 truck and even a city bus. Each car feels distinct in its handling, which is both a blessing and a curse. The game’s physics engine, while fun, feels overly forgiving; cars have an uncanny ability to stay upright no matter how reckless your driving becomes. Compared to Carmageddon‘s weighty, destruction-heavy cars, Midtown Madness feels much cleaner—and tamer.
There’s also damage, but it’s strictly cosmetic. You’ll see cracked windshields, crumpled fenders, and smoking engines, but don’t expect to flatten your car into a tin can. Pedestrians, meanwhile, will always jump out of the way of your vehicle at the last second—a clear move to keep Midtown Madness family-friendly and distinct from its grittier cousin Carmageddon.
Visuals and Sound: ‘90s Vibes Galore
Graphically, Midtown Madness is a product of its time, but it still manages to impress. The textures are detailed, reflections on vehicles are slick, and little touches—like the Doppler effect as cars zoom past you—add polish. Civilian cars are noticeably less detailed to accommodate their sheer numbers, but the opponent vehicles look just as sharp as your own ride.
The game’s biggest visual drawback is its slightly washed-out color palette. Carmageddon 2 had a more vibrant and striking visual style, while Midtown Madness opts for something a bit flatter. Still, when you’re weaving through traffic or barreling off raised bridges, it’s hard to complain.
Final Thoughts: A Must-Play Racer
Midtown Madness may not have the edgy, stunt-heavy physics of Carmageddon, but it more than makes up for it with its open-world charm and chaotic fun. Driving through Chicago at 120 mph—blaring your horn, smashing garbage cans, and dodging police cars—is just as satisfying now as it was in 1999. The game modes are diverse, the vehicles offer a good range of driving styles, and multiplayer (especially Cops and Robbers) elevates the experience into something special.
The novelty of being the most obnoxious driver in simulated America will eventually wear off, but the laughs, thrills, and bridge jumps? Those stick with you. If you missed this gem back in the day, it’s absolutely worth revisiting—because Midtown Madness is still a joyride worth taking.
How to Play Midtown Madness Today
Revisiting Midtown Madness in 2024 takes a little work, but it’s absolutely worth the effort:
- Original Disc on a Retro PC: If you still have the original Midtown Madness disc, you can install it on an older Windows machine (Windows XP or earlier is ideal). It runs best natively on these systems without compatibility tweaks.
- Modern PC with Compatibility Tweaks: For newer systems, you’ll need to use Open1560: A mod for Midtown Madness 1, primarily focused on supporting modern computers and fixing bugs. This tool helps fix resolution issues, color glitches, and compatibility with modern Windows versions.
- Emulation and Virtual Machines: Setting up a virtual machine with Windows 98 or XP via software like VirtualBox or PCem can also provide a near-authentic experience. This option ensures you’re running the game in its native environment without major issues.
Unfortunately, Midtown Madness isn’t currently available on digital platforms like Steam or GOG. Until it gets a re-release (fingers crossed!), the options above are your ticket to experiencing this open-world classic.