11. Espresso-2-Go! - GTA III
https://www.youtube.com/watch?v=BdlAX4nmKHc Chances are you won't remember this one by name - but so labyrinthine and hyper-extended was its structure that you'll be cursing again just after watching the above video. See, once you opened up the entirety of GTA III's map it was an excuse for Rockstar to set missions that spanned the entire length of all three islands, making for suitably epic drives across multiple city blocks - but also setting you up for one hell of a failure if things fell apart at the last second. In this case you were tasked with destroying some market stalls... ones that for no reason other than "It's GTA!" were incredibly hard to take apart. You can see in the video above whoever's playing resorting to blasting them with a rocket launcher like many ended up doing - but all that serves to land you with is an increasingly large wanted level that'll get in the way instead.