What works best for cooling a room - fan pointing in or fan pointing out?

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If the window will open at the top also, place the fan up there blowing out. Open the window at the bottom only slightly to allow some cooler air in, but making the fan push more hot air out, than the window opening is letting cool air in.

As the hottest air is also the highest in the room, this scenario will have the best cooling effect.

If there is another window in the room, open it at the bottom instead of the one with the fan in it.

Be sure to run it all night long and turn it off early in the morning. Do not turn it back on until the air in the room starts to get hotter than the outside air.

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What works best for cooling a room - fan pointing in or fan pointing out?

@ Sumner

Fan pointing in.
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Sorry not correct.
By blowing the air into the room, you are at the same time blowing the heat from the fan motor into the room.

By blowing it out, this extra heat never gets mixed with the room air.

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@ T_Bone
"A neat thing they do in the middle east, they suspend a piece of canvas above the roof to block the sun, and since the canvas is suspended above the roof, the heat from the sun hitting the canvas just blows away, rather than heating the roof."
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Hundred year old houses in the south are designed to work the same way.

High, steep angled roofs with large vents high on the gables allow the heat to escape before the attic heats up enough to transfer into the living space of the house.

Ever see a mobile home with an extra roof about two feet above the mobile home's flat roof and extending out a few feet past the sides? It's an indication the owner knows it will keep it cooler while at the same time protecting the home's flat roof from the eventual leaks they all get. There are quiet a few vacation houses like that at a large lake nearby