This is actually going to be difficult for most English speakers to quantify.
The difference between these two conjugations is all about the sequence of a story. When you tell a story in chronological sequence, the simple past tense is straightforward. You say this happened, and then this happened, and then this happened. But when you are in the middle of this sequence, any explanations that go back in time again would be confusing to just keep using the simple past tense. Let's try an example:
"So yesterday I went to the mall, and while I was there I ran into Kevin. Kevin told me that his sister was pretty mad at him for losing their tickets."
This is a simply story about something that happened in the past. The sequence is easy to follow. Now let's add the next part:
"So yesterday I went to the mall, and while I was there I ran into Kevin. Kevin told me that his sister was pretty mad at him for losing their tickets. He dropped them from his pocket when he pulled out his keys."
If you stay in the simple past tense, this part sounds a little bit confusing. You can probably figure it out by correcting the storyteller in your head, but you have to think about it. Just saying it like this sounds a little like Kevin told the storyteller that his sister was mad at him for losing the tickets, but then Kevin pulls out his keys and the tickets drop out. The listener could think the storyteller is trying to say that Kevin was mistaken and he had the tickets in his pocket the whole time. Let's change that last sentence to past perfect:
"So yesterday I went to the mall, and while I was there I ran into Kevin. Kevin told me that his sister was pretty mad at him for losing their tickets. He had dropped them from his pocket when he pulled out his keys."
This now makes it clear that the storyteller is explaining that, at some point before the storyteller spoke to Kevin, Kevin dropped the tickets from his pocket, which is why his sister was mad.