Physics
It is easier to roll a barrel full of coal tar than to pull it because

coal tar is a liquid and it flows in the barrel when it is rolled
the rolling friction is much less than the sliding friction
more surface area of the barrel is in contact with the road when it is pulled
the full weight of the barrel comes into play when it is pulled

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Physics
Should cars have bumpers that collapse under impact?

No, since it would be very expensive to get the car repaired
Yes, since they help to absorb the impact of a collision and keep the occupants safe
No, since the colliding car would then ram into the occupants and kill them
Yes, since the offending car should get damaged and pay for the mistake

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