Teddy still hasn't found what he's looking for

It would be weird to finish something and say it was totally perfect, the son of Richard and Linda Thompson, one-time golden …

It would be weird to finish something and say it was totally perfect, the son of Richard and Linda Thompson, one-time golden couple of British folk-rock, tells Tony Clayton-Lea

'MOST PEOPLE that are involved in any kind of artistic endeavour, if they have any kind of grounding in reality, will surely question whatever it is they work on. You can be pleased with something, but you can still look at it in a critical light. It's the usual self-doubt thing; it'd be weird to finish something and say it was totally perfect. I don't think that's possible. You don't ever want to be too pleased with yourself, do you?" It isn't too surprising to discover that Teddy Thompson - who by coincidence just happens to be the son of Richard and Linda Thompson, one-time golden couple of British folk-rock - is a glass-half-empty person.

In his early 30s, London-born Teddy moved to Los Angeles when he was 18; it was at this reasonably tender age that he decided the songwriting life was for him, and in what has proven to be something of a serendipitous move, he linked up with the offspring of another lauded 1960s/1970s folk singer - Loudon Wainwright III's kids, Rufus and Martha Wainwright. Well connected to the LA singer-songwriter scene and lusty denizens of same, the Wainwright siblings took Teddy under their collective wing and showed him the ropes.

Record deals came and went - one with Virgin for his 2000 self-titled debut, and then with Universal with 2005's Separate Waysand last year's Up Front Down Low. Thompson's most recent album, A Piece of What You Need, is, he says, his "last chance with this label", which could be construed as fatalistic if it weren't for the fact that he's naturally the self-doubting sort.

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"I've only ever known commercial failure," he imparts, half-glum, half-joking, "so I'm not particularly concerned or down about whether or not the new album sells millions. I approached it a bit differently, but not from the point of view of the songs - I wrote them as I felt I should and would. I didn't give too much thought to the sound of the record, either, until the songs were finished. Having said that, when we came to record it I knew I'd have to do quite well with it if I were not to get dropped. Which is fine, but I thought I may as well go for it - spend the budget, get a good producer in, make the pop record I always wanted to make and go for broke."

As in his lyrics, in life Thompson is a realist: "We'd like to think that it was all about the creativity, all about the music, and that you should follow your heart. Well and good, I agree, but musicians have to eat and sleep and pay the rent, too. So it's somewhat naive to go the artists' route; I have one eye on making a living and doing what I want to do, but not to the point that it makes me do anything I don't want to do. I don't feel that I'm compromising anything here - I have always wanted to make a pop record; it's not as if I was playing acoustic and someone popped in and said I had to make a pop record. So hopefully the stars are all aligned and I'm making my big pop record when everyone else wants me to."

The difference between pop music in general and Teddy Thompson's version is that his default setting is firmly stuck on despair. The songs on A Piece of What You Needare imbued with a sense of reinvention, and reference the kind of soaring melodies and chord changes that bring to mind the very best of, say, Neil Finn. The lyric content, however, is self-critical, self-questioning, occasionally self-loathing. What gives with the unhappy-bunny stance?

"Well, that's a good enough assessment," avers Thompson, before diving into the answer. "I'm quite a self-critical person and always have been, and I tend to look on the dark side a bit. I always dreaded going back to school on Monday the minute I finished school on the Friday, rather than thinking about it on the Sunday evening. The unexamined life is not worth living, and I choose to self-examine. It's important to stress, however, that I don't walk around being mopey all the time, I just tend to write about it. I also feel that all the songs of pain, love and heartbreak are much more powerful emotions to me than giddiness and excitement. That's just the way it is; I'd always preferred these types of songs and they're what I've always gravitated towards."

Thompson is at pains to emphasise that just because he has embraced reasonably commercial production values (via name producer Marius De Vries, who has previously assisted Madonna, Massive Attack and David Gray) and, as he has said, is going "for broke" doesn't mean that he was willing to relinquish his core creative aims.

"What's different about the new record is not so much the subject matter or the style in which I write - me, me, me, and aren't I sad, etc - but that we took the music into a more upbeat setting. I wasn't trying to change me but just trying for a different environment. In relation to the record, people have been throwing about words such as 'slick', 'streamlined' and 'polished', which are not really the words I'd like to use, because they tend to have negative connotations. But that said, the album is a bit more of that - it's more 'realised', I reckon. The sonic details, the instruments and the arrangements are a lot more together, too."

If he's anything like his father - one of rock music's most rugged individualists - Teddy Thompson knows that the only way to get ahead in life is to travel on a singular path, regardless of consumer tastes and cultural dictates. Unsurprisingly, he takes advice from very few people.

"And certainly not when I'm making a record, because it's quite hard to do when you're in the midst of it. I didn't bring the songs back home, play them to people and ask what they thought. I probably played rough mixes to my mum, but she just said to turn the vocals up. Good advice, in a way, and very straightforward, but technically useless! I try and separate the recording process from the live process, because most of the time the studio and the live environment are two very different things; by the same token I wasn't going for a record that sounded as if we were playing live."

So to self-critical, self-questioning, self-loathing and self-doubting, can we add self-challenging? It would seem we can. "I tend to be one of those people that can be a bit lazy, but then I berate myself for being that way, so I try to put myself into a place that is challenging. I met those challenges head-on here, and I'm glad to say that this album fulfilled and exceeded my expectations."

• Teddy Thompson plays Whelan's, Dublin, on Sept 27. A Piece of What You Needis out on Universal records. www.teddythompson.com