Guess That Record

Guess That Record returns with Jackson interviewing fellow Canadian Jill Hennessy! An actress and musician who's been achieving success since the early 1990s, Jill has appeared in numerous films and shows. She's best known for her roles on shows like Law & Order, and Crossing Jordan. As a musician, she's released two studio albums and performed at Lilith Fair. In this episode, Jackson and Jill talk about her Canadian upbringing...

It's the milestone 50th episode of Guess That Record, and Jackson's special guest is Alexa Ray Joel! The daughter of Billy Joel and Christie Brinkley, Alexa has followed in her father's footsteps to become a successful musician performing her own original music. In this episode, Jackson and Alexa talk about her upcoming releases, her musical influences, and what it's like to perform with her father at major venues like Madison Squa...

Guess That Record returns with Jackson interviewing Midge Ure! Hailing from Scotland and having been active in music since the early 70s, Midge is best known for serving as the frontman for the band Ultravox. The group had a string of hit singles on the UK charts in the 80s including "Vienna," and "Dancing With Tears in My Eyes." Midge is best known for his collaboration with Bob Geldof, co-writing "Do They Know It's Christmas?" an...

This episode of Guess That Record has Jackson interviewing drummer Chris Maas! Hailing from Luxembourg, Chris has been active in the music business for over 20 years working with artists like Mumford & Sons. Since 2024, he's been the drummer for Sting as a member of the new STING 3.0 band. In the interview, Jackson and Chris talk about growing up in Luxembourg, the grind of finding work as a musician, and what's been the most s...

This episode of Guess That Record has Jackson speaking with the incredible Steve Porcaro! A keyboardist and founding member of Toto, Steve has been playing on hit songs since the 1970s. Outside of Toto, he's worked with Yes, Don Henley, and Michael Jackson. For the latter, Steve wrote one of the biggest hits off of the Thriller album, "Human Nature." In this episode, Jackson and Steve talk about his upbringing in a musical family, ...

This episode of Guess That Record has Jackson speaking with music industry veteran Andy Factor of Everloving Records! Andy got his start at Virgin Records, where he played a key role in the company's A&R during the 1990s. He then left to start Everloving, which has released albums by Jack Johnson, Metric, and The Jack Moves. In the episode, Jackson and Andy talk about how he got started at Virgin, what it was like to start Ever...

The new episode of Guess That Record has Jackson speaking with podcasting veteran Ralph Sutton! A seasoned podcast and pop culture commentator with two decades of experience in front of the mic as a TV and radio host. Currently, Ralph is the host of the hit comedy podcast The SDR Show, and in 2016 founded the GaS Digital Network, which reaches 4 million listeners a month across 22 shows. Prior to that he created his own nationally ...

Guess That Record returns with Jackson interviewing Pete Muller! After achieving success in quantitative finance, he found himself yearning to fulfill his creative urges. Balancing fatherhood, marriage, and running a company, he continued to write and perform – eventually releasing a series of albums that would lead to dates with the likes of John Oates, Lisa Loeb, Jimmy Webb, Livingston Taylor, and Paul Thorn, along with fes...

On this episode of Guess That Record, Jackson is joined by Billy West! One of the greatest voice actors of all time, Billy has appeared in numerous productions over the course of his storied career. He is best known for his work on Futurama, voicing the lead characters of Fry, Professor Farnsworth, and Dr. Zoidberg. He also appears in Space Jam as Bugs Bunny, as well as shows like Doug, and The Ren & Stimpy Show. He's also a mu...

The first Guess That Record of 2026 features Jackson speaking with Kenny Aronoff! Named one of the 100 greatest drummers of all time by Rolling Stone, Kenny remains one of the most in demand performers behind the kit in the music industry. He's worked with John Mellencamp, John Fogerty, Sammy Hagar, The Rolling Stones, and many more. In the episode, Jackson and Kenny talk about recording hit songs with John Mellencamp, his unexpect...

On Guess That Record, Jackson welcomes successful bassist Matt Bissonette to the podcast! Matt has been active in the music industry since the 1980s, becoming one of the most in demand bass players for some of the biggest names in music. Matt has had the chance to work with Elton John, Ringo Starr, David Lee Roth, Rick Springfield, and many more. In this episode, Jackson and Matt talk about his early days in music, hearing stories ...

Guess That Record returns with music executive Ruchir Mohan joining Jackson for a great conversation! Ruchir is a member of 1916 Enterprises, a management company representing artists, songwriters, and producers. Some of Ruchir's clients include rapper Tommy Genesis, and Morgan Wallen songwriter James Maddocks. In the episode, Jackson and Ruchir talk about his journey in the music business, and what it takes to be a manager in toda...

On this episode of Guess That Record, Jackson speaks with longtime record producer and composer Fred Mollin! Fred has been active in the music business since the 70s. His big break came in 1977, when he co-produced Dan Hill's smash hit "Sometimes When We Touch." The single reached #3 on the Billboard Hot 100, and was nominated for a Grammy. Fred has since gone on to work with Billy Joel, America, Jimmy Webb, Johnny Mathis, and Kris...

On this episode of Guess That Record, Jackson gets to speak with Phil Manzanera of Roxy Music! An early member of the group, Phil played guitar on all of Roxy Music's albums which included hit songs like "Love Is the Drug," "Jealous Guy," and "More Than This." In 2019, Phil and the band were inducted into the Rock and Roll Hall of Fame. Phil has also worked extensively with Pink Floyd and David Gilmour, co-producing David's "On An ...

On this episode of Guess That Record, Jackson is joined by fellow Canadian Geordie Brown! Hailing from Dartmouth, Nova Scotia, Geordie is a singer and actor who got his start in theatre. His big break was securing the lead role in Foreigner's "Jukebox Hero: The Musical" which premiered in 2019. Geordie has continued his collaboration with Foreigner, as he will be joining the band as the guest vocalist for their upcoming fall 2025 t...

Guess That Record returns with Jackson interviewing guitarist Frank Hannon! Frank is a co-founder of the successful band Tesla, who had a string of hits in the late 80s and early 90s which includes songs like "Love Song" and "Signs." While continuing to perform with Tesla, Frank has also performed as a solo artist, with his new album "Reflections" available now. In the episode, Jackson and Frank talk about how Love Song was an unco...

Guess That Record returns with Jackson interviewing the great Neil Giraldo! Best known for serving as the guitarist and producer for his wife Pat Benatar, Neil has worked on all of her records, which includes hit singles like "Love Is a Battlefield," "We Belong," and "Heartbreaker." Neil has also worked with many other artists including Kenny Loggins, Steve Perry, and Rick Springfield. With the latter, he played on the number one s...

On this episode of Guess That Record, Jackson speaks with Carlton "Santa" Davis! Santa is one of the most successful reggae drummers of all time, working with artists like Bob Marley, Peter Tosh, Jimmy Cliff, and many more. He's currently the drummer for Ziggy Marley, a role he's held for nearly 20 years. In this interview, Jackson and Santa talk about his upbringing in Jamaica, stories from his career, and a lesson in reggae drumm...

Guess That Record returns with Jackson interviewing Canadian radio host Raina Douris! Raina is currently the host of World Cafe, NPR's flagship music program. Since becoming host in 2019, Raina has had the chance to interview major stars like Bruce Springsteen, Ringo Starr, Sting, and many more. In the episode, Jackson and Raina talk about her move from Canada to the US, Raina's best interviews, and what it takes to produce an epis...