I would say his best album was 1972's Sail Away, with the two runners-up being 1974's Good Old Boys and 1999's Bad Love, and there are plenty of great songs scattered among his other albums, not to mention among the tracks he wrote for others but never sang himself. For my part, while I wouldn't say that every one of his songs hits the mark, many of them are truly brilliant. Even John Cleese, who admitted almost complete ignorance about popular music (he couldn't even remember what band Mick Jagger was in), said he was a fan of Randy Newman. Mark Knopfler cited Newman's songs as an inspiration for "Money for Nothing". Several artists have recorded entire albums of Newman's songs, most notably Harry Nilsson on Nilsson Sings Newman. Paul McCartney, Brian Wilson, Peter Gabriel, Tony Banks and many others have said they are fans of his work. While Randy Newman doesn't have the level of fame of the Beatles, the Rolling Stones or Bob Dylan, he is highly regarded by many critics and artists. But perhaps his best work has appeared on his albums, which despite a relative lack of commercial success (the major exception being the song "Short People") have been critically well regarded.
He was nominated for an Academy Award 15 times before finally winning one on his 16th nomination, and he now has 2 Oscars out of 20 nominations (as he said, "my percentages aren't great").
In his early years he wrote songs for other artists, and in the last few decades he has become known primarily as a composer of movie soundtracks, including films like The Natural, Meet the Parents, Awakenings, Ragtime, Cars, Monsters Inc. He has been writing songs professionally since his late teens. Randall Stuart Newman, best known as Randy Newman, was born into a family of musicians (his uncle Alfred won nine Academy Awards for his film work) on November 28, 1943. November 28 is the birthday of a very different American popular music artist, one who is a contender for the greatest living American composer of popular song. November 27 was the 70th anniversary of the birth of Jimi Hendrix.