''Midtown Madness'' is a racing game developed for Windows by Angel Studios and published by Microsoft. A demo version was released via download on May 1, 1999, and the entire game was released on May 27, 1999. A sequel, ''Midtown Madness 2'', was released in September 2000, and the final addition to the series, ''Midtown Madness 3'' was released in June 2003 for the UsefulNotes/{{Xbox}}. Set in UsefulNotes/{{Chicago}}, the goal of ''Midtown Madness'' is to win street races and obtain new cars.
!!Tropes appearing:
* ConsoleCameo: In ''Midtown Madness 3'', certain pedestrians can be seen carrying boxes branded with the original Xbox logo.
* {{Dissimile}}: In ''Midtown Madness 3'', each loading screen shows the race map and a caption. One caption says "It's like a square, only it's not."
* HaveANiceDeath: If you drive into the lake or the river in ''Midtown Madness'', you get the message "Sleep with the fishes!", and, in ''Midtown Madness 2'' as well driving in San Francisco, meanwhile in London it adds the message "More tea, vicar?".
* InvulnerableCivilians: The pedestrians have incredible dodging skills, though in the first game, you could turn the weather to snowy and drive down the sidewalks of Lakeshore Drive to force them to dive into Lake Michigan. They would welcome death after that.
* KentBrockmanNews: ''Midtown Madness 2'' has at least one announcer like this (out of three or four); one of their race-opening lines ends in "... probably because I'm not wearing any pants!"
* LemmingCops: The cops in the series are ridiculously single-minded in their attempts to run you off the road, including crashing through other traffic.
* ManInAKilt: One of the random bits of starting encouragement dialogue in London in ''Midtown Madness 2'' is a Scotsman saying "If you can't feel the wind under yer kilt ye aren't going fast enough! Whaddaya ''mean'' yer not wearin' a kilt?!"
* MinusWorld: Using the drive on water and speed mods for ''Midtown Madness 2'', one can explore areas beyond the roads of London and San Francisco. Because these areas were never meant to be explored, there are holes in the terrain, flat areas hidden from view during normal gameplay by buildings, and in the San Francisco map, part of Alcatraz and Marin can be visited using the drive on water hack.
* OptionalTrafficLaws: The game specifically has the pedestrians run out of the way if they're on the street, or flatten themselves against a building, making it impossible to run anyone over. If you do obey traffic laws (speed limit, lanes, lights, etc), you are left alone by the authorities. Breaking any of these laws results in the cops chasing you mercilessly.
* RampJump: The series has rising bridges that the player can jump over, as well as trailer ramps scattered throughout the cities.
* {{Ramprovisation}}: In ''Midtown Madness 2'', you can jump from one embankment of the Thames to the other by use of strategically placed ramps in the Tower of London, and a (convenient) boat in the middle of the river.