Four-time Grammy-winning songwriter Jimmy Webb has topped the charts from pop to country to disco numerous times with interpretations by some of the industry’s greatest, from Glen Campbell to Art Garfunkel to Linda Ronstadt and covers by everyone from Guns n’ Roses to Josh Groban to Little Big Town. Since Webb’s Grammy sweep in 1968 when his own “Up, Up and Away” and “By the Time I Get to Phoenix” vied for Song of the Year (and “Up” won) to the use of his “Do What You Gotta Do” in Kanye West’s “Famous,” the man often praised as “America’s Songwriter” remains an icon in popular music — and continues to challenge his artistic boundaries with projects like a classical nocturne. His most famous songs are touchstones for a generation yet remain timeless — “MacArthur Park,” “Wichita Lineman,” “Worst That Could Happen.”

Now in his touring show “An Evening with Jimmy Webb” and his literary memoir, The Cake and the Rain (St. Martin’s Press; now in paperback and audiobook) Webb brings fans of his music a unique connection to their favorite songs, revealing the stories behind his hits as far back as his first songwriting job at Motown through a career trajectory that took a teen preacher’s son from a farm town in Oklahoma to the top of his longed-for profession, with pitfalls and blessings in equal measure between.

In concert, the man who gave the world what has been called “the first existential country song” (“The Highwayman”) and confounded generations of radio listeners with the brilliance of a lyric about a cake left out in the rain enhances his virtuoso performance of iconic tunes with riveting tales of the inspiration behind some of pop music’s biggest songs and singers, and a humorous tour into the days and nights of a songwriting prodigy, a lesson in pop culture, an insider perspective on the musical giants of the Sixties, the Rat Pack heyday, the London Mods, Laurel Canyon and more, told by a charming yarn spinner who hasn’t lost sight of his roots despite decades of international fame. More than a concert, an evening with Jimmy Webb in performance is a master class you can sing along with.

As Webb performs five decades of music on this tour, the songs and stories resonate with his longtime fans as well as new devotees introduced to the music through covers by modern chart toppers including Five for Fighting (“All I Know”), Rumer (who stormed the UK in 2012 with her take on “P.F. Sloan”) or any number of reinterpretations of “Wichita Lineman” by R.E.M., Urge Overkill, Keith Urban, Homer Simpson, and more. Songs made famous as recorded by an impressive and ever widening range of artists are discovered anew with revelations by the man who first brought them to life on the piano.

A close read of Webb’s memoir reveals gems like the genesis of songs like “P.F. Sloan,” and “Mac Arthur Park” as the details are woven into the stories he tells of his days in London and Los Angeles, navigating a world that fueled his lyrics and nearly broke him on more than one occasion. His songwriting style expanded in the longer format of a memoir, Webb gives the reader access to pivotal moments during the music scene of the 1960s and 70s — riding Mr. Sinatra’s private elevator for a one on one meeting, elbow to elbow with Elvis, an urgent request from John Lennon, the first meeting that sparked his decades-long partnership with Glen Campbell and more.