Place the eggs in a pot and cover with cold water. Bring to a boil, then remove from heat, cover, and let sit for 12 minutes.
Drain the eggs and run them under cold water until cool enough to handle. Peel and slice each egg in half lengthwise.
Scoop the yolks into a mixing bowl. Add the mayonnaise, mustard, salt, pepper, and paprika. Mash until smooth.
Spoon or pipe the yolk mixture back into the egg white halves.
Slice each black olive crosswise to create 8 rounds. Press one olive slice gently into the center of each filled egg to form a pupil.
Cut the cucumber lengthwise into four long pieces, then trim the sides to create shallow boat shapes. Set one finished egg half into each cucumber boat.