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Midtown Madness is a racing game developed for Windows by Angel Studios and published by Microsoft. A demo version was released via download on February 1, 1999, and the entire game was released on February 27, 1999. A sequel, Midtown Madness 2, was released in April 2000, and the final addition to the series, Midtown Madness 3 was released in June 2002 for the Xbox. Set in Chicago, the goal of Midtown Madness is to win street races and collect new cars.
Unlike many racing games, which restrict the player to a race track, Midtown Madness offers an open world recreation of Chicago. This setting was developed by Microsoft and described as offering "an unprecedented degree of freedom to drive around in a virtual city". Players can explore the city via one of several modes, and can determine the weather and traffic conditions for each race. The game supports multi-player races over a local area network or the Internet. Overall, the game received positive reviews from gaming websites. Reviewers generally praised the gameplay, though some criticized the graphics.
Midtown Madness features four single-player modes: Blitz, Circuit, Checkpoint, and Cruise. In Blitz, the player must reach a destination within a time limit; in Circuit, the player races other vehicles; in Checkpoint, the game adds the complication of other traffic, such as police cars and pedestrians; and in Cruise, the player simply explores the city. Players have a choice of up to ten vehicles, although only five are available at the start. To unlock the other cars, players must achieve goals such as winning a certain number of races. Before a race, if the player has previously won the race, they can change the race duration or the weather, which can affect vehicle performance. Checkpoint mode allows players to set the frequency of traffic, police cars, and pedestrians.
The city is modelled after Chicago, including many of its landmarks, such as The 'L', Sears Tower, Wrigley Field, and Soldier Field. Its streets feature many objects that the player can crash into, such as trash bins, parking meters, mailboxes, and street lights. In Checkpoint, traffic is regulated by traffic lights, but the player is under no obligation to obey them.
Midtown Madness supports multi-player games via local area network, Internet, or serial cable connection. Multi-player mode was originally supported by Microsoft's MSN Gaming Zone, though this service was retired on June 19, 2006. It was supported by similar services such as GameSpy Arcade and XFire, via DirectPlay. Multi-player includes a Cops and Robbers mode, inspired by the television program World's Deadliest Police Chases. This is a capture the flag-style game in which players form two teams; each team must steal the opposing team's cache of gold and return it to their own hideout.
Midtown Madness was one of the first games that Angel Studios (now Rockstar San Diego, part of Rockstar Games) developed for the PC. Microsoft was following up on their previous Madness computer games, Motocross Madness and Monster Truck Madness. According to project director Clint Keith, the idea behind the game came to two Microsoft employees while they were "trying to cross a busy Paris street". They proposed their idea to Angel Studios, who were attempting to sell Microsoft a 3D vehicle simulator. Angel Studios were initially hesitant to accept Microsoft's offer, as it "seemed too large a challenge to pull off". After agreeing, Angel Studios chose Chicago for the setting because it is the site of several famous car chases, such as those in the film The Blues Brothers. To ensure that the city was recreated faithfully, Angel Studios had Chicago residents playtest the game. PC Gamer reported a consensus that the recreation was mostly accurate, though Angel Studios had relocated landmarks to enhance the gameplay.
Angel Studios and Microsoft included ordinary cars in addition to the "overpowered Italian sports cars" often seen in racing games. The developers had to obtain permission from manufacturers to use the likenesses of the vehicles; Microsoft thus received permission from Volkswagen for the New Beetle and from Ford for the Mustang and F-350. The decision to make only half the cars available at the outset was to promote a "spirit of competitiveness". Microsoft also told Angel Studios not to allow players to hit pedestrians. After deciding against rendering pedestrians in two dimensions, Angel Studios developed 3D pedestrian models that could run and jump out of the way. Angel Studios included an option to remove pedestrians, as they do not alter gameplay but may significantly affect system performance when in a group; consequently, the game does not require a 3D graphics card.
A demo version was released for download on May 1, 1999. It featured three vehicles (a Mustang, Panoz Roadster, and bus), and all four driving modes. The demo also included features that would be scrapped in the full version, such as the ability to send billboards flying. In December 1999, Angel Studios reported that they were considering a map designer for players, but such customization never materialized. The finished game was released on May 27, 1999.
The game is distinctly different from other racing games — IGN noted the difference from the Need for Speed series—because of what Microsoft called "an unprecedented degree of freedom to drive around in a virtual city". Clint Keith said the idea behind an "open space" game was to make the gameplay more diverse, and to add an "element of discovery", such as the shortcuts players can take to reach the finish line first. Gary Whitta described the game as open racing: "you still have checkpoints to hit [but] you don't have to follow the A-B-C-D standard to do it".