Earbuddy's 10 Best Albums of 1999

Jeff Tweedy and the late Jay Bennett built it from layer after layer of overdubs, with Bennett’s Mellotron in place of strings, while the drummer and bassist were largely left out. Tweedy was reading Henry Miller and William H. Gass and his marriage was under strain; in his memoir he calls it the record his wife finds hardest to hear. Eighth in Pazz & Jop.

Made by the original four-piece with Kevin “She’kspere” Briggs and Kandi Burruss, Rodney Jerkins and Missy Elliott among the producers, and opened by a Godfather spoof that sets out its commandments of relationships. “Bills, Bills, Bills” and “Say My Name” were their first US No. 1s, and LeToya Luckett and LaTavia Roberson learned they were out of the group from the “Say My Name” video.

His first studio album since The Black Rider in 1993, and the first release on Anti-, the label Epitaph set up to put it out. Waits wrote most of the songs with his wife, Kathleen Brennan, and they produced it together; he described the idea as somewhere between surreal and rural. It won the Grammy for Best Contemporary Folk Album and came fifth in Pazz & Jop.

Will Oldham’s first album as Bonnie “Prince” Billy, made with a small band: his brother Paul recorded it and played bass, Colin Gagon added piano and accordion, and David Pajo played guitar on “Song for the New Breed”. Johnny Cash recorded the title song for American III: Solitary Man in 2000, with Oldham singing alongside him. Pitchfork ranked it sixth of the year.

Named after Chinua Achebe’s novel and recorded at Electric Lady in New York, where the Soulquarians were making records of their own. Jill Scott co-wrote “You Got Me” and sang its hook until the label asked for a bigger name, Erykah Badu; Eve raps on it, and it won a Grammy in 2000. J Dilla produced “Dynamite!”. Twelfth in Pazz & Jop.

Moby made it in his Manhattan apartment, building “Honey”, “Find My Baby” and “Natural Blues” around voices from Alan Lomax’s field recordings, which he found on a box set a friend gave him. At first the only offers were licensing deals, and in the end all 18 tracks went to films, TV shows or adverts. It topped Pazz & Jop and went on to sell 12 million copies.

His solo debut, a year after the Black Star album with Talib Kweli. He plays bass, congas and, on “Rock N Roll”, drums, next to beats by DJ Premier on “Mathematics” and Ali Shaheed Muhammad of A Tribe Called Quest on “Got”. He sings “Umi Says” rather than raps it, and “New World Water” warns of a coming shortage of clean water. He now performs as Yasiin Bey.

Apple wrote the full title as a 90-word poem after readers’ letters mocked her following a 1997 Spin cover story. At 444 characters it broke the record for the longest album title, which Chumbawamba’s 865-character The Boy Bands Have Won beat in 2008. Jon Brion produced it. Seventh in Pazz & Jop, and 19th on Pitchfork’s list of the best albums of the 1990s.

Stephin Merritt had the idea in a Manhattan piano bar while the pianist played Sondheim: a hundred love songs for a stage revue with four drag queens. He settled on 69, three discs of 23 songs that hop from genre to genre, and Merge put them out in September 1999. Merritt has said it is about love songs, not love. Second in Pazz & Jop.

Made over the best part of two years with Dave Fridmann at Tarbox Road, his studio in Cassadaga, New York; by his account it began as a stereo version of the four-disc Zaireeka. The strings are samples played live on keyboards, not an orchestra, and “Waitin’ for a Superman” is Wayne Coyne facing his father’s slow death from cancer. Second on Pitchfork’s list of 1999.