Pink Floyd had an extraordinarily large back catalog since they were a band that was passionate about creating music and was focused on the future. It is nearly hard to fully unpick since it is highly twisted, textured, and impenetrable. When one thread of their musical creation is pulled out of the fabric of their body of work, it seems as though a whole other web of work to explore takes its place. Which songs does the band’s main member, the amazing guitarist David Gilmour, think are the best? There are fifteen studio albums to pick from.

Gilmour has probably answered this difficult question with a wry smile many times in the past. Most musicians would just brush it off, but Gilmour has occasionally talked about his thoughts on his favorite tracks from the original acid-rockers. To be fair, the man will have contributed so much to Pink Floyd’s output that selecting a few tracks to name his favorites would be like choosing a sonic Sophie’s selection. Unlike that situation, though, there’s a strong probability his response will vary each time it’s posed.

The band’s singer and guitarist, who replaced Syd Barrett at the start of their extensive 55-year adventure, once selected six songs from a big collection of amazing work that he found most appealing. Gilmour would argue that the selections are a group of songs that have stood the test of time and continue to seem as natural to him now as they did when they were originally created. Generally speaking, an artist is more impressed by the concept of timeless quality. They have a strong probability of deserving favoritism if their creations continue to hold true decades after they were first made.

To be honest, it might be difficult to determine which Pink Floyd songs are Gilmour’s favorites. Throughout his rocky career with the band, the singer battled creative blockages and internal conflicts with Roger Waters, which frequently left him with a slightly bitter aftertaste. Considering his own successful solo career, it must get old to constantly respond to inquiries about Pink Floyd from fans. But that’s what happens when you belong to one of the most iconic groups in history.

Fortunately, Gilmour was interviewed by Billboard in 2006, and during a lengthy interview in which he covered nearly every aspect of his career to date, Gilmour did respond to the most requested question: which Pink Floyd songs were his favorites? Even though he named some Floyd classics as his favorites, he acknowledged that “there’s lots of them.”

“Shine On You Crazy Diamond” and “Wish You Were Here” are standout tracks, Gilmour said, picking two songs from the Wish You Were Here album. The tunes are undoubtedly among Floyd’s greatest. In addition to being a great piece of music, “Shine On You Crazy Diamond” also contains a heartfelt message at its core. It was written as a remembrance of Syd Barrett, who left the group after failing to overcome his crippling mental health problems. He starts in a threatening and dark manner before eventually taking his style to new heights and paying homage to the late great artist in an appropriate way.

Another Pink Floyd song that stands out is “Wish You Were Here.” Gilmour’s successful 12-string entrance, the captivating acoustic solo, and the pedal steel guitar that cuts through the entire production set the tone for this captivating song. Though the lyrics were written by Waters, Gilmour made the most of the sentimental wording.

The guitarist chose two of the band’s most well-known songs, and he may have guaranteed the trio of Pink Floyd hits when he chose “Comfortably Numb,” which is perhaps the band’s most well-known song from The Wall and a song that Gilmour particularly likes.

Choosing some of his best solos, Gilmour mentioned Pink Floyd as the source of his greatest moment, describing ‘Comfortably Numb’ as the apex of his and the band’s live performances. “It was a fantastic moment, I can tell, to be standing up on there, and Roger’s just finished singing his thing, and I’m standing there, waiting,” Gilmour recalls.

He added, “I’m in pitch darkness, and no one knows I’m there yet. And Roger’s down, and he finishes his line, I start mine and the big back spots, and everything going on and the audience, they’re all looking straight ahead and down, and suddenly there’s all this light up there and they all sort of—their heads all lift up and there’s this thing up there, and the sound’s coming out and everything. Every night there’s this sort of ‘[gasp!]’ from about 15,000 people. And that’s quite something, let me tell you.”

The majority of Pink Floyd fans would probably agree with the tracks that were originally mentioned. While Gilmour did not name all of those songs as his personal favorites, he did eventually concede defeat and acknowledge that “there are lots of them” when he said, “One of my favorite all-time Pink Floyd tracks is ‘High Hopes’ from The Division Bell.” He also added a few more songs for good measure, like “The Great Gig in the Sky” and “Echoes.”

It was inevitable that “High Hopes” would end up on Gilmour’s list. This song serves as the basis for a large portion of A Momentary Lapse of Reason and marks one of the first times he collaborated extensively on the lyrics with his wife, Polly Samson. Gilmour said, “I started writing things and looking to her for an opinion, and gradually, as a writer herself and an intelligent person, she started putting her oar in, and I encouraged her.”

Great Gig in the Sky, one of Pink Floyd’s most well-known songs, obviously makes Gilmour happy. Given how closely it is linked to his late buddy and Floyd keyboardist Richard Wright, there’s a strong probability that Gilmour will always love this song. His last option, “Echoes,” is inextricably linked to Wright as well. A genuinely rich composition, it has some of Gilmour’s finest band work, including a technically impressive yet emotive solo that few could match. But since Wright passed away, Gilmour will never be able to perform it: “There’s something that’s specifically so individual about the way that Rick and I play in that that you can’t get someone to learn it and do it just like that. That’s not what music’s about.”

The remainder of the interview, which was done at the time to support his solo tour, provides an honest look at Gilmour. When questioned if he ought to be performing at larger places in order to please fans, he honestly responded: “I can’t help other people’s frustrations. I don’t owe people anything. If people would like to come to my concerts, I’d love them to come. And if they like the music that I make, I love that too. But I do not make music for other people. I make it to please myself.”

It’s the kind of unwavering dedication to their craft that has allowed Gilmour and Pink Floyd to maintain their status as purists.

Regarding his legacy, Gilmour reflected: “Oh! [Long silence] Legacy? What’s a legacy? I think our music will continue to be played for a while. Then it will be forgotten like everything else will be forgotten. How long will that take? A hundred years, a thousand years, a million years? I have no idea. This is not something I think of very much.”

David Gilmour’s favourite Pink Floyd songs:

• Shine On You Crazy Diamond’
• ‘Wish You Were Here’
• ‘Comfortably Numb’
• ‘High Hopes’
• ‘The Great Gig in the Sky’
• ‘Echoes’