OpenTTD 1.11
Oh man, this is still my favorite game 27 years later.<p>Chris Sawyer (the original developer) is one of those OG 10x developer. Built an entire game + AI + windowed GUI in Assembly in 1992! Even before Windows 3.11 came out.<p>I still remembered my first impression back in 1994 distinctly.
I can open 20 different windows in Transport Tycoon and each window follows its own respective vehicle like a drone cam.<p>The GUI windows themselves can be resized smoothly and piled on top of each other. Something that older version of Windows couldn't do.<p>Also, the game was fairly small in size and incredibly stable.<p>I thought to myself, this developer was a mega genius!