[Much like the shooting yourself in the foot list, these jokes are showing its age. If you can come up with clever ways in which it can be improved, expanded, etc., please let me know.]

• MS-DOS
  • You get in the car and try to remember where you put your keys.
• Windows
  • You get in the car and drive to the store very slowly because attached to the back of the car is a freight train.
• Windows NT
  • You get in the car and write a letter that says “Go to the store”. Then you get out of the car and mail the letter to your dashboard.
• Mac OS
  • You get in the car to go to the store, and the car drives you to church.
• UNIX
  • You get in the car and type grep store. After reaching speeds of 200 miles per hour en route, you arrive at the barber shop.
• BSD
  • You get in the car, whereupon AT&T slaps you with a lawsuit, and you get to sit in your garage for a year or two.
• OS/2
  • After fueling up with 6000 gallons of gas, you get in the car and drive to the store with a motorcycle escort and a marching band in procession. Halfway there the car blows up, killing everyone in town.
• Taligent/Pink
  • You walk to the store with Ricardo Montalban, who tells you how wonderful it will be when he can fly you to the store in his Lear jet.
• Amiga
  • You get in the car and tell it to go to the store, and it takes you to a shopping mall on the Moon.
• S/36 SSP (mainframe)
  • You get in the car and drive to the store. Halfway there you run out of gas. While walking the rest of the way, you are run over by kids on mopeds.
• OS/400
  • An attendant locks you into the car and then drives you to the store, where you get to watch everybody else buy filet mignons.
• VAX/VMS
  • You use up tremendous amounts of gas to go very slowly and only get to see an image of the store.