Twenty-five years ago today – that’s literally a quarter of a century – a brand-new racing game arrived on Windows 98 and Windows 95 PCs. Midtown Madness was an absolute blast and quickly became one of my most-played games of the year. With the millennium fast approaching, nothing was more fun than tearing up the streets of Chicago, getting into scrapes with the police, and taking part in some wild and dangerous races against the AI!
Midtown Madness celebrating its 25th anniversary makes me feel so incredibly old… but I’m glad to have the opportunity to talk about one of my favourite racing games of that era. Midtown Madness did something that I hadn’t really seen before in a video game – it opened up its entire city and let me drive wherever I wanted, however I wanted… even if that meant off-roading across grassy parks, scaring pedestrians on the pavement, or jumping over an open drawbridge! Two-and-a-half years before Grand Theft Auto III would take that series’ titular mayhem to an open-world environment, Midtown Madness was doing something remarkably similar.
Although it didn’t feel that way at the time, when I look back at Midtown Madness with a quarter of a century of hindsight, it feels like a gaming landmark; an important title that did the “open world chaos” thing in its own way before some of the better-known titles in that space. In 1999 it felt incredibly new and innovative; a game that seemed to take the chaos of the likes of Grand Theft Auto but made it fully 3D. Looking back, it feels like a half-step between 2D games, racing games, and the kind of fully open-world titles that were right around the corner.
I’d also place Shenmue in that same category: the “almost-open-world” games that were the progenitors of the format. Released the same year as Midtown Madness, but in a completely different genre, Shenmue was also an early pioneer of many of the features that open-world games continue to take advantage of to this day. 1999, it seems, was one of the most important years in the development of open-world titles!
I don’t have the receipt, unfortunately, but I think I must’ve picked up Midtown Madness within a week or two of its launch. I remember playing it that summer and into the autumn; it was one of the only up-to-date PC games that I owned at the time. I’d seen a preview of it in one of the gaming magazines that were prominent on newsagents shelves in those days, and it just looked like such chaotic fun that I could hardly wait to get my hands on it! I didn’t have a PC racing wheel or any fancy equipment – and as you’ll know if you’ve ever tried it, playing a racing game with a mouse and keyboard is painful! But that didn’t stop me, and I must’ve logged dozens upon dozens of hours in Midtown Madness… in between studying and working my part-time job, of course!
Taking on races was the only way to unlock half of the vehicles in the game – the other half were available right from the start. So I definitely took part in as many races as I needed to in order to unlock the likes of the city bus and the GTR-1 racecar! But where I had the most fun with Midtown Madness was driving around the city in free-roam mode – both as chaotically and as calmly as possible! The game’s rendering of downtown Chicago – while undeniably dated by today’s standards – felt like a technological marvel in 1999, and I loved every minute of exploring the city.
This wasn’t my first encounter with the Windy City. I’d been a huge fan of the medical drama ER in the second half of the ’90s, following every episode and every season as they were broadcast here in the UK. I think by mid-1999 we were on Season 3 or 4 of the show, which at that point still featured George Clooney and Julianna Margulies in starring roles! But because I felt a familiarity with Chicago – from its Lake Michigan waterfront to its “L” trains that ran on elevated tracks above the streets – I felt even more drawn to this digital recreation of the city. In fact, it was one of the first digital recreations of a real-world city that I can remember spending much time with.
Going into the millennium, I’d have had Midtown Madness’ in-game map pretty much committed to memory! I could find my way from one side of the map to the other, stopping to see the sights along the way – and the game recreated some of Chicago’s most famous landmarks. I’ve already mentioned the “L” – Chicago’s elevated metro system. But there was also the Sears Tower skyscraper, Navy Pier on the Lake Michigan shorefront, the planetarium, the Wrigley Field baseball stadium, and even the airport! All of these were a ton of fun to race through and explore.
Although the game came with options for tuning the physics engine and car performance, I didn’t spend too much time tinkering. The default settings seemed to work well enough, and I was always reluctant to mess about with them too much! Midtown Madness performed very well on the PC that I had at the time, with none of the bugs and glitches that seem to plague games today. Perhaps I’m looking back with rose-tinted glasses when I say that… but I genuinely cannot remember any bugs or performance issues that got in the way of the fun.
Obviously when you compare Midtown Madness with a racing game from the 2020s, like Forza Horizon 5, or open-world car games like Grand Theft Auto V, it feels incredibly dated. Graphics that felt great at the time look blocky in 2024, with far too few polygons, and the game has the overall look of a title from the late ’90s. The turn of the millennium would see advancements in graphics that would make Midtown Madness 3 – released less than four years later – look an awful lot better.
And in terms of the game’s world, the relatively low numbers of vehicles on the road and pedestrians on the pavements doesn’t feel right for a massive metropolis like Chicago. There’s also a lack of diversity – there are only a handful of vehicle types and pedestrian models, and you’ll pretty quickly see all of them if you spend much time with Midtown Madness.
But those were the restrictions that game developers had to work with in 1999, and obviously an open-world city like Cyberpunk 2077 or a racing title like Gran Turismo 7 is going to surpass Midtown Madness in every way a quarter of a century later. That’s not what makes it such a special title – and no one is really asking it to go toe-to-toe with modern racing and open-world titles.
Instead, we have to view Midtown Madness – and, by extension, video games in general – as a stepping-stone. The premise or DNA of later titles like Test Drive Unlimited, Project Gotham Racing, or the Forza Horizon series is present in Midtown Madness, and the game was among the first to demonstrate open-world and free-roaming elements in a racing game, as well as the merits of letting players cause chaos and create their own fun. Those gameplay ideas have become commonplace in the years since Midtown Madness was released – and now extend far beyond the racing genre.
For me, Midtown Madness is an incredibly nostalgic title. I’d love to be able to play it again – but getting it to work on a modern PC, even with a virtual desktop running Windows 98, is a pain. The game can be easily found online in its complete form, but it would be fantastic if Microsoft could work with a company that specialises in porting retro games to modern systems and give it a proper re-release. After 25 years, I think Midtown Madness deserves better than to be left behind! Many other retro titles have been brought back over the past few years, so there’s almost no reason not to do it!
I had such a great time with Midtown Madness as the millennium approached. It was one of the games I encountered in the late ’90s that seemed to be pushing boundaries and trying something different – and something genuinely engaging and fun. It felt like a step up from basically any other racing game I’d played up until that point, and one that definitely captured and held my attention.
As we mark the milestone 25th anniversary of Midtown Madness, I look around at open-world titles and racing games and still see a number of features that I first encountered in this landmark title. It was a truly fantastic game that gave me a ton of fun and with which I made some wonderful memories.
All that remains to say is this: happy anniversary, Midtown Madness!
Midtown Madness is currently out of print, but copies may be available second-hand. Midtown Madness remains the copyright of Microsoft, Angel Studios, and/or Rockstar San Diego. Some screenshots and still frames courtesy of LGR’s retrospective review and The Racing Madness Wiki. This article contains the thoughts and opinions of one person only and is not intended to cause any offence.
Trekking with Dennis 