Randy Newman has earned perpetual status on the short list of America’s best pop songwriters. Like the case of fellow laureate Warren Zevon and his darkly comic “Werewolves of London,” Newman spent a period pigeonholed by the success of his satirical-but-insightful 1977 No. 2 single “Short People,” and then the half-smirking MTV-era hit “I Love L.A.” The novelty of those tracks was eventually overshadowed by the warmth and companionship of 1996’s “You’ve Got a Friend in Me,” written for Disney-Pixar’s “Toy Story” film.

Those rarified singles may have household-name status, but the depth and quality of Newman’s five decades of output are what have truly made him a trusted resource for singers, filmmakers and music fans with a penchant for a sharp-witted piano man. His music for films has earned Academy Awards and Grammy Awards dating back to 1985’s “The Natural.” Countless artists have recorded his songs, including gospel music hero Mavis Staples. The local favorite recorded Newman’s heartbreak ballad “Losing You” for 2010’s Jeff Tweedy-produced album “You Are Not Alone.”

Next week, Newman arrives for two nights at City Winery to play career-spanning sets and introduce material from his new album. Online ticket purchasers will receive their choice of a physical or digital copy of “Dark Matter,” Newman’s first album since 2008’s “Harps and Angels.” The new songs are both catchy and challenging, demonstrating Newman’s Tin Pan Alley craft and willingness to employ unconventional methods. As with his best-known work, sentimentality and cynicism rub shoulders.

The Great Debate” gathers a cast of debatable experts to argue big issues from the perspectives of science and faith. Eventually, the characters in the song turn their critical gaze upon Newman himself. It’s the pop music equivalent of Paul Auster’s metafiction novel “City of Glass.”

One “Dark Matter” song skewers Vladimir Putin. Another gives voice to blues legend Sonny Boy Williamson, jealously protecting his legacy from the Great Beyond. Newman’s tender side emerges on “She Chose Me,” a satisfied and grateful opposite number to “Losing You.” Newman may delight in playing the wise guy or old crank, but it makes his forays into warmth heart resonate all the more.

* Randy Newman, 8 p.m. Oct. 18-19, Metro, 1200 W. Randolph. Admission: $100+; citywinery.com.

Jeff Elbel is a local freelance writer.