I found some interesting stuff here, might not make sense if you're not familiar with these operating systems though.
If Operating Systems were Airlines
DOS AIR All the passengers go out onto the runway, grab hold of the plane, push it until it gets in the air, hop on, jump off when it hits the ground again. Then they grab the plane again, push it back into the air, hop on, etcetera.
WINDOWS '95 AIRLINES The terminal is very neat and clean, the attendants are all very attractive and the pilots very capable. The fleet is immense. After your plane arrives 6 months late, you begin to wonder why it has not arrived yet. Your jet takes off without a hitch, pushing above the clouds, and at 20,000 feet it crashes without warning.
MAC AIRWAYS The cashiers, flight attendants, and pilots all look the same, feel the same and act the same. When asked questions about the flight they reply that you don't want to know, don't need to know, and would you please return to your seat and watch the movie.
OS/2 SKYWAYS The terminal is almost empty, with only a few prospective passengers milling about. Airline personnel walk around, apologising profusely to customers in hushed voices, pointing from time to time to the sleek, powerful jets outside the terminal on the field. They tell each passenger how good the real flight will be on these new jets and how much safer it will be than Windows Airlines, but that they will have to wait a little longer for the technicians to finish the flight systems.
FLY WINDOWS NT All the passengers carry their seats out onto the tarmac, placing the chairs in the outline of a plane. They all sit down, flap their arms and make jet swooshing sounds as if they are flying.
WINGS of AS/400 The airline has bought ancient DC-3s, arguably the best and safest planes that ever flew and painted "747" on their tails to make them look as if they are fast. The flight attendants, of course, attend to your every need, though the drinks cost $15 a pop. Stupid questions cost $230 per hour, unless you have SupportLine, which requires a first class ticket and membership in the frequent flyer club.
VMS AIRLINES The passengers all gather in the hanger, watching hundreds of technicians check the flight systems on this immense, luxury aircraft. This plane has at least 10 engines and seats over 1,000 passengers. All the passengers scramble aboard, as do the necessary complement of 200 technicians. The pilot takes his place up in the glass cockpit. He guns the engines, only to realise that the plane is too big to get through the hangar doors!
UNIX EXPRESS Each passenger brings a piece of the airplane and a box of tools to the airport. They gather on the tarmac, arguing constantly about what kind of plane they want to build and how to put it together. Eventually, they build several different aircraft, but give them all the same name. Some passengers actually reach their destinations. All passengers believe they got there.