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Livingston Taylor celebrates a half-century of live performance via his impressive LIVe: 50 Years of Livingston Taylor. The five-CD, DVD, and photo book box set is the result of years of careful archiving and travels from 1969 to 2016. The 87 pieces include material that covers a wide range of emotions and moods, from expected love songs and examples of Taylor's singular humor as well as his deep appreciation for other writers. Those who purchase the physical edition are treated to the 2018 documentary film Livingston Taylor-Life Is Good, directed by Tracey Anarella.

Perhaps more striking than the song list itself is the sense of intimacy one gains from hearing these tracks. Taylor is a patient and precise performer as much as he is an exacting writer and, one senses that by the time the collection winds to a close neither a note nor a word is wasted. Listeners can observe a similar precision as they cast their ears back through Taylor's previous recorded output, starting with 1971's eponymous LP and 1978's Three Way Mirror on down to 2014's Blue Sky and 2017's Safe Home.

An accomplished storyteller and author who has been on faculty at Berklee College of Music for 30 years, Taylor is generous in conversation and thoughtful with his answers. He moves between subjects such as his musical family (including his brother James and late brother Alex), his close relationship with his audience, and one of his current fascinations, battery power. Preparing to leave for a working trip to Vietnam, Taylor says that he's loaded up on reading on the matter and that it's the kind of thing that motivates him to continue writing.

But what else would we expect from an artist who has penned appreciations for the Wright Brothers and who delves into historical narratives with the authority and authenticity of a scholar?

Your career is largely based on live performance. Were you immediately comfortable once you got on the stage?

I've always enjoyed being in front of a group of people. It's something my family is comfortable doing. My brother James is a fine performer and loves his audience. My sister Kate and my brother Hugh, my oldest brother, Alex, our parents, were all very comfortable in giving extemporaneous speeches. It's just a trait of our family that we're comfortable on stage.

When you started playing, were you coming at it with your songs or were you performing material from other people?

As soon as I started playing, I started writing. I had other people's songs, but I had a bulk of my own. That was the foundation. I've been a writer since the age of 16.

How long did it take you to figure out what your songs would be about?

One tends to write, particularly in the early days, about things that are immediate. Being in love, being out of love. The prime directive being the perpetuation of the species. That leads you to write a whole lot of songs about relationships. As you get older, such things have less importance. I found myself branching out and writing historical songs. I found myself writing songs about the Civil War or the Wright Brothers.

How much have you seen your audience change along the way?

The ones that didn't like my choices in music self-eliminated long ago. The other people are with me like the journeys that I go on. They understand that these are not going to be terribly radical journeys and that I, of course, dip into the familiar stuff. But they're excited to know where I want to go today.

Tell me about your incorporation of humor in songs and performances.

I never saw myself as funny, but I am funny. I'm funny because people are surprised at how relaxed and comfortable I am in their presence. I like them. I'm glad to be there. It's an absolute delight, on the way to a show, to think about my audience. I like to think about the fact that I'm going to see them and we're going to spend time together. That gives me great pleasure and comfort. I feel humbled by people who have supported my music for a lifetime. It's the highest compliment.

You have some cover songs on this new collection, and I wonder if there's a difference between wanting to cover a song and being able to.

A song I've always wanted to cover is Frank Sinatra's "That's All". I love that song. I can sing it well, and I could put interesting chord changes behind it. But, lyrically, it's got an insurmountable problem: In the last verse, you have:

If you're wondering what I'm asking in return, dear
You'll be glad to know that my demands are small
Say it's me that you'll adore for now and evermore, that's all, that's all

That's not a small request! That's a huge request to make of somebody. I can't reconcile those things. It's important to me that a song can be reconciled, not only melodically, but lyrically. I haven't been willing to re-write that last verse. Sometimes I'll do that. Sometimes I'll go into a less-known song, and I'll change a few things around. Tweak them ever-so-slightly.

You probably have songs of your own where the relationship changes.

I think it does. In my early writing, because I lacked skills as a songwriter that I have today, the songs are more difficult to sing. Today, I can write with a great economy of melody and chord progression and lyric.

How did you become a faculty member at Berklee College of Music?

I had a friend who was head of the performance division, and he asked me if I would like to teach a course. I said, "You bet!" I was on it in a nanosecond. I've been teaching there for 30 years.

What is it that you present to students and hope they walk away with?

Nobody needs you. You need them. They're only buying it because it makes them feel better about themselves. If an audience doesn't feel better about themselves after leaving your show, they're not going to come back.

You're a pilot. Where did your love of planes come from?

When I was about four or five years old, there was an ad on television, animated, for a cereal called Sugar Jets. A kid, my age, ate some of that cereal and flew, and I thought, "That's a great product!" I got my mother to buy me some of this cereal, and I ate it with the full expectation that I would be able to fly. But it was lodged in my brain that flying would be a good idea. As soon as I got sober enough and rich enough, I started flying.

What's next for you? Are you always writing?

I'm leaving for Southeast Asia tomorrow with my wife. We're making music for a group that's traveling through Vietnam and Cambodia. I was thinking about what I wanted to read, and I realized that I don't know enough about battery technology. I know the history of the battery but, given how important batteries are going to be, coming up, I realized that I needed to know more about them. That's typical: Finding a subject that interests me and wanting to develop expertise in it.