Loudon Wainwright appeared laid back and relaxed on the Bristol stop of his extensive British tour. Commanding a large stage with no more than his voice and a pair of acoustic guitars, the Carolina-born singer-songwriter struck a warm and conversational tone, cherry-picking a set from his four-decade archive of wry and bittersweet ballads.

Partly thanks to the patronage of John Peel, Wainwright has long enjoyed a loyal following in Britain, where he lived for much of the 1980s and 1990s. The growing success of his musical offspring, especially eldest son Rufus, may also have boosted his profile in recent years. Despite the long-running Freudian psychodrama between them, which sometimes spills over into caustic song lyrics, father and son now enjoy cordial relations and play similar-sized venues.

Like dozens of his late 1960s peers, Wainwright was once hailed as a successor to Bob Dylan. In truth, his plaintive voice has more in common with Neil Young, while his droll observations are closer to Randy Newman in style. Wainwright’s comic side dominated for much of this set, sometimes at the expense of musical quality. One tune, a slender ditty about snowy weather, dated back to his tenure as a regular on comedian Jasper Carrott’s TV show Carrott Confidential in the late 1980s.

But such trifling asides detracted a little from Wainwright’s most potent songs, which explore the emotional terrain between humour and pain with a novelistic eye for detail: songs such as Dreaming, a hushed and exquisite paean to the power of poetic fantasy over prosaic reality.

Equally touching was the singer’s elegant reconstruction of his long-lost grandfather from a faded photograph in The First Loudon, or his memories of his mother’s death in the deceptively cheerful White Winos and the achingly tender Homeless.

Because Wainwright has always written from the perspective of his own baby-boomer generation, his lyrics have become increasingly obsessed with age and mortality. Indeed, his Bristol set was peppered with ruefully funny reflections on turning 60, as he did last year. One such tune, Doin’ the Math, was taken from his new album Strange Weirdos, a soundtrack to the forthcoming Hollywood comedy Knocked Up, in which the singer also has a small role. Further extracts from the album included Grey in LA and Valley Morning, both sweetly sardonic vignettes of life in Wainwright’s current home of Los Angeles.

The singer’s daughter Lucy Wainwright Roche, who is serving as his opening act for the tour, also duetted on several numbers. Roche’s honeyed tones came into their own on their encore reading of At the End of a Long Lonely Day, a back-porch country ballad shot through with sepia-tinted nostalgia. However fractious their family soap opera may be offstage, the Wainwright dynasty still make sweet music together. Touring tonight at St David’s Hall, Cardiff

Editor's choice

• The 100 Best Films of the Decade
• 70 facts you didn't know about Marvel
• The 50 Biggest Movies Of 2010