Let's break down and solve the expression step by step:

$(-2)[(-3) - (-4)(-5)]$

1. Evaluate the multiplication inside the brackets: $(-4) \times (-5) = 20$

2. Substitute this result into the expression: $(-2)[(-3) - 20]$

3. Simplify the expression inside the brackets: $(-3) - 20 = -23$

4. Now, multiply: $(-2) \times (-23) = 46$

So, the value of the expression is:

$\boxed{46}$

Would you like more details on any step, or have any questions?

Here are 5 related questions to explore further:

1. What is the general rule for multiplying negative numbers?
2. How does order of operations affect solving more complex expressions?
3. What happens if we change the signs in the multiplication?
4. How can we apply this concept to solve algebraic equations?
5. How do parentheses impact the calculation process?

Tip: Always follow the order of operations (PEMDAS: Parentheses, Exponents, Multiplication/Division, Addition/Subtraction) when solving mathematical expressions!