Cary Baker was a Chicago music writer and fanzine creator who made a good impression on R.E.M. and wound up running publicity for the band and its label, I.R.S. Records. There he also worked with the Go-Go’s, General Public, Fine Young Cannibals, the Alarm, Concrete Blonde and Timbuk 3, whom he got booked onto Saturday Night Live. After R.E.M. left the label, Baker did too, moving to Capitol Records and working with Paul McCartney, Tina Turner, Bonnie Raitt, the Smithereens and other big names. Eventually he formed his own firm, Conqueroo (a Chicago blues reference), and represented acts including the one that changed his life as a college student: Cheap Trick. Baker recently retired after 42 years of adventures in the publicity game, and he has stories to tell.

When Adrian Belew was brought in to record his mind-bending guitar solos on what became Taking Heads’ landmark 1980 album Remain in Light, he felt an unprecedented amount of freedom. He was presented not with almost-finished songs but unstructured grooves that felt like vast open spaces for him to color in. That he did, brilliantly, and Belew and Jerry Harrison of Talking Heads are now revisiting this album with a live tour. Of course, Belew’s resume covers a lot more ground, including guitar wizardry with Frank Zappa, David Bowie, Paul Simon and Nine Inch Nails, his stint as lead singer/songwriter of King Crimson and his own solo career. How did each of these collaborations stretch him? And was he really asked to replace David Byrne in Talking Heads?

Peter Case is a singer-songwriter who has covered a tremendous amount of ground, both physically and stylistically, over a long, impressive career. He played pop-punk with the Nerves, power-pop with the Plimsouls (“A Million Miles Away”), Americana as a solo artist before Americana was a thing, and many styles since then, including the pounding piano blues of his upcoming Doctor Moan. Here he recalls days of scraping by as a street musician, tells jaw-dropping L.A. stories featuring the Go-Go’s and Jerry Lee Lewis, recounts how Blondie came to cover the Nerves’ “Hanging on the Telephone,” recalls the Plimsouls' appearance in Valley Girl and relives his dreams, disappointments (with a cameo by the label exec who also rejected Wilco’s Yankee Hotel Foxtrot) and triumphs, This is a great conversation for songwriters and music fans alike.

Denny Laine was the one full-time Wings member whose last name isn’t McCartney—as well as a Rock & Roll Hall of Fame inductee with the Moody Blues. Wings went through multiple lineup changes during the 1970s, and for Band on the Run and much of London Town, the band was down to just Paul and Linda McCartney and Laine. Which Wings lineup does Laine consider the strongest? What was co-writing with McCartney like? How did they come to write and record “Mull of Kintyre,” and were they surprised when it became, at the time, the biggest-ever British hit single? Did they work better without an outside producer? Did McCartney’s cannabis arrest in Japan mark the end of Wings? Laine co-wrote “No Words” but has plenty of good ones in this Caropop conversation.

David Pasquesi is an actor who makes an impression even if you don’t know his name. He brightens The Book of Boba Fett as the sly, untrustworthy Majordomo. He’s the smiling, conniving Veep ex-husband Andrew Meyer. He’s the ever-searching alchemist Blaise St. John on the cult-fave series Lodge 49. You also may have caught him on She-Hulk: Attorney at Law (another cheerful scoundrel), At Home with Amy Sedaris (Knife Man Tony!) and in movies including Groundhog Day. For more than 20 years, he has performed the wholly improvised TJ and Dave show with fellow Second City alumnus T.J. Jagodowski. How does Pasquesi balance acting and improv? Why does he play so many shifty characters? Will he attend Star Wars conventions now? Pasquesi is quick-witted and revealing in this Caropop conversation, recorded live at the club Space in Evanston. Don't miss actor Michael Shannon's question at the end.

Robyn Hitchcock has been writing surreal, catchy, muscular, gentle, haunting, melodic pop rock songs from his late-'70s/early '80s work with the Soft Boys through his excellent new album, Shufflemania! He still sounds young yet digs into aging and mortality in his music and this conversation. He also discusses whether he absorbs or echoes such influences as Syd Barrett and John Lennon, how his collaboration with XTC's Andy Partridge worked, what his live-performance pet peeve is and whether inspiration more often finds him or forces him to seek it out. Hitchcock remains as inventive, imaginative and thoughtful as they come.

Brendan Benson is an accomplished solo artist who also happens to co-lead a popular band, the Raconteurs. He'd released three albums of tuneful, smart rock when he played an unfinished song for his Detroit friend Jack White. The White Stripes frontman completed it, they recorded it with another band’s rhythm section, and a supergroup was born, along with its first hit, “Steady, As She Goes.” Now Benson lives in Nashville, where he recorded his excellent eighth solo album, Low Key, and he also collaborates with other musicians, some country, some not (including Robyn Hitchcock). How do those co-writing gigs work? Why can they be embarrassing? Has Nashville rubbed off on his songwriting? Does he consider his work to be autobiographical? Will he ever tour again on his own or with the Raconteurs? Benson is as insightful in conversation as he is in song. (Photo by Guillaume Lechat.)

Mastering engineer Kevin Gray returns to Caropop to break down mono vs. stereo and other issues of sound. Gray has been remastering Blue Note’s acclaimed Tone Poet and Classic Vinyl series, including separate mono and stereo releases of John Coltrane’s Blue Train. Which does Gray prefer and why? Are there time periods when mono is likely to be superior to stereo and vice versa? How are the rules different for jazz and rock? What accounts for a recording’s soundstage—how spread out the instruments sound?

Gray also discusses whether the Beatles revamps are revisionist history, whether electronically reprocessed stereo is ever any good, the differences between the Tone Poet and Classic Vinyl releases and his work at Cohearent Audio on funky ’70s recordings for Craft Records’ Jazz Dispensary label and Intervention’s stunning reissue of Joe Jackson’s Night and Day. Then there's his own label's upcoming first release: a jazz album recorded at his home studio modeled after legendary engineer Rudy Van Gelder's Hackensack set-up.

Singer-songwriter Vonda Shepard played herself on TV’s Ally McBeal, performing at the characters’ favorite piano bar, and she co-wrote and sang the show’s theme song, “Searchin’ My Soul.” But even with multiple Ally McBeal-tie-in albums, there’s been much more to Shepard’s career than the show. She performed her first gig as a 14-year-old, toured in Rickie Lee Jones’ band and duetted with Dan Hill on the 1987 smash “Can’t We Try.” Years of development with Warner Brothers led to her self-titled debut album, but the label dropped her, Ally McBeal creator David E. Kelley boosted her, and she kept writing songs and releasing albums, including this year’s Red Light, Green Light (produced by husband Mitchell Froom). She reflects on her career's many twists and turns in this lively, wide-ranging Caropop conversation. (Photo by Greg Shappell & Nick Leopold.)

Guitarist Jeff “Skunk” Baxter was an original Steely Dan member who played on the band's indelible first three albums: Can’t Buy a Thrill, Countdown to Ecstasy and Pretzel Logic. Those are his memorable solos on “My Old School” and “Rikki Don’t Lose That Number.” When Steely Dan quit touring, he found more success with the Doobie Brothers and eventually brought in singer Michael McDonald, who pushed that band in a more soulful, keyboards-heavy direction. Skunk left to do more studio and touring work and was inducted into the Rock & Roll Hall of Fame with the Doobies. After all these years, he finally released his first-ever solo album, Speed of Heat. Oh, and in his "day job," he games out war scenarios for the U.S. government. He has a lot to reel in in this ear-opening Caropop conversation.