Pictures:

Akiva Lane
General
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Why did Jim write a last will and testament?

Because where there is a will there's a way.

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Akiva Lane
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What does an orchestra and a destructive mob have in common?

They both have violins.

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Akiva Lane
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If the second hand on a clock measures seconds, what does the first hand measure?

Either minutes or hours, but we're not sure.

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Akiva Lane
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What animal is similar to a tree that looks like a pole?

Poultry.

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Akiva Lane
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When is a hot cup cold?

When there isn't something hot in it.

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Shane Ronay
General
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What are the odds that this man will slim down?

A fat chance.

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Akiva Lane
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In a group of rabbits, how far are they from each other?

A hare's breath.

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Shane Ronay
General
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Which Russian leader used delay tactics as a military strategy?

Stallin'

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Akiva Lane
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What expression refers to an insect in the late spring?

Bee that as it May.

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Akiva Lane
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What do you call worrying about the complications of losing money in a real estate complex?

A complex complex about a complex.

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General
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When the pessimist says 'It can't get any worse', what does the optimist say?

It can!

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Akiva Lane
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If the rule is "I before E except after C", why is the word Weird different?

Because the word is Weird.

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