But when given the chance to talk to Armatrading ahead of her upcoming New Zealand shows, I can't help telling her how much brain power I've spent on that song.
She chuckles and quick as a whippet she has an answer for me. "The song means, don't go out with that person, come out with me. It's much more intriguing to say 'Drop the pilot' than 'don't go out with that person, come out with me'. It doesn't bring up questions really, does it? But if you say, 'Drop the pilot' it does. It makes you think."
I'm not sure I love Armatrading more for solving a near life-long debate in my head or for what she tells me next - that it was the first and only song she wrote with the deliberate intention of creating a hit.
"I sat down to write a hit single. It's not something I do, but I did at that point. I thought 'I wonder what it'd be like? I wonder what it'd be like to purposefully sit down to write a hit single?' I mean, I didn't purposefully sit down to write Love and Affection. I just wrote the way I write," she says.
"Some people might say, 'Why didn't you keep doing that?' But I've had a lot of success with songs. It's not that Drop the Pilot is the only success I've had. The albums have always done well - certainly all the early albums.
"And Into the Blues in 2007 did incredibly well, so it's not like I can't do it by writing the way I write. It's just that time, I wanted to do this experiment. And it worked."
For me, it's further proof of the Armatrading genius and another reason she's such an enigma. The woman who shunned the celebrity spotlight for decades intentionally sat down and wrote a hit because she felt like it, and because she could. And nailed it.
So it's sad to think these upcoming Auckland, Wellington and Christchurch shows could be the last time we see Armatrading down this way.
But if anyone deserves to hang up the long-haul touring boots, it's her. She has traversed the globe countless times and her current tour stretches over about 18 months and takes in a dizzying number of countries.
"The tours are long. This is actually why it's my final, or my last major world tour. A short tour is six months and that's a long tour," says the British singer, who turned 64 on Tuesday.
"By the time the tour finishes at the end of December next year, I'll be 65," she says, laughing.
On the bright side, Armatrading is performing solo - something she has rarely done in her 40-odd-year career - and has deliberately selected more intimate venues for that reason.
"I've always had a band, right from the start. I've done the odd gig on my own, but you'd have to go back to 1973," she says.
It has taken her a few gigs to feel comfortable with standing all alone on stage.
"It is nerve-racking but the more I do it, the less nerve-racking it becomes. You know, just like normal nerves, which I always had going on stage anyway.
"But I have been absolutely enjoying it. It feels quite natural. And I'm confident in what I've written. I'm confident in my playing," she adds.
I'm just as confident that Armatrading's so-called Farewell Performance will be one of those nights you remember forever.
• A Farewell Performance: Joan Armatrading. Town Hall, Great Hall, Auckland on Wednesday, The Opera House, Wellington on Thursday. Her concert at the Isaac Theatre Royal in Christchurch on Friday is sold out.
