History in Picture and Video
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Bailey Family Singers
As a youngster in Portland, Oregon, Bob’s musical talents were developed playing for and singing with his family, The Bailey Family Singers. He absorbed the sounds of gospel music and found his talent for arranging as he imagined the songs he heard differently and introduced those ideas to the family group.
As a youngster in Portland, Oregon, Bob’s musical talents were developed playing for and singing with his family, The Bailey Family Singers. He absorbed the sounds of gospel music and found his talent for arranging as he imagined the songs he heard differently and introduced those ideas to the family group.
Animal House
While a student at the University of Oregon, Bob and a group of musicians known as Shinola began performing in the area. John Belushi happened into one of the bars and heard the group. Robert was subsequently cast in the film, National Lampoon’s Animal House.
WATCH HERE: Video from Animal House
While a student at the University of Oregon, Bob and a group of musicians known as Shinola began performing in the area. John Belushi happened into one of the bars and heard the group. Robert was subsequently cast in the film, National Lampoon’s Animal House.
WATCH HERE: Video from Animal House
New Hope
In his third year of college, Bob left Eugene and joined Cam Floria’s group, New Hope, which served as his introduction to contemporary Christian music. With New Hope, he toured the globe and began to delve deeper into songwriting.
In his third year of college, Bob left Eugene and joined Cam Floria’s group, New Hope, which served as his introduction to contemporary Christian music. With New Hope, he toured the globe and began to delve deeper into songwriting.
The PTL Singers
After returning home from the New Hope tour, Bob received a call from The PTL Club offering him an audition as one of the The PTL Singers. He joined Jim and Tammy Faye Bakker’s burgeoning ministry and became the first Black singer in the group, paving the way for talents like BeBe and CeCe Winans.
WATCH HERE: Tammy Faye Bakker “We’re Blest”
After returning home from the New Hope tour, Bob received a call from The PTL Club offering him an audition as one of the The PTL Singers. He joined Jim and Tammy Faye Bakker’s burgeoning ministry and became the first Black singer in the group, paving the way for talents like BeBe and CeCe Winans.
WATCH HERE: Tammy Faye Bakker “We’re Blest”
The Debut Album
In 1979, Bob signed his first recording contract as a solo artist with the Good Life Company. His debut album, Looking Forward, was released in 1980 and re-released in 1981 by Triangle Records, distributed by the Benson Company.
In 1979, Bob signed his first recording contract as a solo artist with the Good Life Company. His debut album, Looking Forward, was released in 1980 and re-released in 1981 by Triangle Records, distributed by the Benson Company.
Looking Forward
With arrangements by Bob Krogstad, Howard McCrary and David Diggs and a cast of musicians that included in-demand session players like Larry Williams and Ken Wild of Seawind and Paul Leim and the McCrarys (on background vocals), and a duet with CCM’s First Lady, Reba Rambo, Looking Forward introduced Bob as an artist in his own right.
LISTEN HERE: https://www.youtube.com/watch?v=TbQGXZ5B2cM
With arrangements by Bob Krogstad, Howard McCrary and David Diggs and a cast of musicians that included in-demand session players like Larry Williams and Ken Wild of Seawind and Paul Leim and the McCrarys (on background vocals), and a duet with CCM’s First Lady, Reba Rambo, Looking Forward introduced Bob as an artist in his own right.
LISTEN HERE: https://www.youtube.com/watch?v=TbQGXZ5B2cM
On The Road
Bob promoted Looking Forward by hitting the road and performing at Christian music festivals, conventions like the Christian Booksellers Association, and churches internationally. After leaving PTL, he moved to Nashville in 1981.
Bob promoted Looking Forward by hitting the road and performing at Christian music festivals, conventions like the Christian Booksellers Association, and churches internationally. After leaving PTL, he moved to Nashville in 1981.
Tales From The Road
While on the road, Bob did the work of being, in many cases, the first Black person many congregations had ever come in contact with. Read more about some of these experiences in his 2022 interview with gospel music historian, Tim Dillinger.
https://godsmusicismylife.substack.com/p/bob-bailey-uniquely-me
While on the road, Bob did the work of being, in many cases, the first Black person many congregations had ever come in contact with. Read more about some of these experiences in his 2022 interview with gospel music historian, Tim Dillinger.
https://godsmusicismylife.substack.com/p/bob-bailey-uniquely-me
Christian Television
Christian television was a primary vehicle through which the public became aware of Bob's music. While Christian radio was not as willing to play his music, Christian television outlets like 100 Huntley Street and smaller stations around the country opened their doors to Bob, giving him a place to share his work.
Christian television was a primary vehicle through which the public became aware of Bob's music. While Christian radio was not as willing to play his music, Christian television outlets like 100 Huntley Street and smaller stations around the country opened their doors to Bob, giving him a place to share his work.
Nashville
Shortly after moving to Nashville, Bob signed with 19th Street Productions as a writer and artist. There, he worked to further cultivate his talent as a writer, collaborating with dozens of writers including Raymond Brown and Holly Dunn.
Shortly after moving to Nashville, Bob signed with 19th Street Productions as a writer and artist. There, he worked to further cultivate his talent as a writer, collaborating with dozens of writers including Raymond Brown and Holly Dunn.
I'm Walkin'
His 1983 release, I’m Walkin’, produced by David Diggs, reflected his growth as a songwriter and artist with his own unique vision of how Christian music could be presented. Recorded with Los Angeles’ session musicians like Jai Winding, Paul Jackson Jr., Ed Greene, Bill and Tamara Champlin, Richard Page, Steve George, I’m Walkin’ was predicted to have a home within the still-quite-segregated world of CCM.
WATCH HERE: https://youtu.be/1d6qaRHvHrs
His 1983 release, I’m Walkin’, produced by David Diggs, reflected his growth as a songwriter and artist with his own unique vision of how Christian music could be presented. Recorded with Los Angeles’ session musicians like Jai Winding, Paul Jackson Jr., Ed Greene, Bill and Tamara Champlin, Richard Page, Steve George, I’m Walkin’ was predicted to have a home within the still-quite-segregated world of CCM.
WATCH HERE: https://youtu.be/1d6qaRHvHrs
Dove Nomination
After a year of trying to break the album in both CCM and gospel markets, the label divested from the project citing their inability to find a market for it, despite a Dove nomination for the album’s title song in the Song of the Year category in the 1984 awards. After terminating Bob from the label, Grammy nominations were announced and I’m Walkin’ was nominated alongside the most groundbreaking and definitive albums of 80s CCM including Steve Taylor’s Meltdown, Michael W. Smith’s debut album and Leon Patillo’s The Sky is the Limit.
After a year of trying to break the album in both CCM and gospel markets, the label divested from the project citing their inability to find a market for it, despite a Dove nomination for the album’s title song in the Song of the Year category in the 1984 awards. After terminating Bob from the label, Grammy nominations were announced and I’m Walkin’ was nominated alongside the most groundbreaking and definitive albums of 80s CCM including Steve Taylor’s Meltdown, Michael W. Smith’s debut album and Leon Patillo’s The Sky is the Limit.
On the Road with Cynthia Clawson
Bob toured with Cynthia Clawson—continuing to support I’m Walkin’ without a contract—and dove deeper into songwriting. The two filmed a television special at PTL in 1985 which aired on The PTL Network. He performed "Rainy Day Christian" from I'm Walkin' and talked about his departure from The PTL Singers in 1981. https://youtu.be/jSIHHpQrtHI
Bob toured with Cynthia Clawson—continuing to support I’m Walkin’ without a contract—and dove deeper into songwriting. The two filmed a television special at PTL in 1985 which aired on The PTL Network. He performed "Rainy Day Christian" from I'm Walkin' and talked about his departure from The PTL Singers in 1981. https://youtu.be/jSIHHpQrtHI
Bring It To Jesus Certificate
Bob found particular synergy with Cynthia’s accompanist, arranger and writer Raymond Brown (also a 19th Street Productions staff writer) with whom he wrote almost a dozen songs. “Bring It to Jesus,” a song they wrote along with Bobby Jones & New Life’s musical director Derrick Lee became a #1 CCM hit in 1987 for Cynthia Clawson. Other artists to record Bob’s songs during this time included The Staple Singers, Philip Bailey and Vernessa Mitchell among others. https://youtu.be/bt-bhoVkxqo
Bob found particular synergy with Cynthia’s accompanist, arranger and writer Raymond Brown (also a 19th Street Productions staff writer) with whom he wrote almost a dozen songs. “Bring It to Jesus,” a song they wrote along with Bobby Jones & New Life’s musical director Derrick Lee became a #1 CCM hit in 1987 for Cynthia Clawson. Other artists to record Bob’s songs during this time included The Staple Singers, Philip Bailey and Vernessa Mitchell among others. https://youtu.be/bt-bhoVkxqo
Crossing Over
In 1988, Bob signed with Airborne Records and, with producer Bobby Daniels, crafted his first mainstream album. With a cast of singers and musicians who all had innovative ideas about what being a contemporary Christian meant, Bob Bailey was in-step with albums of the time, like Amy Grant’s Unguarded, Tramaine Hawkins’ The Search is Over and Kathy Troccoli’s Images. The album’s lead single, “Project Girl,” went into regular rotation on the Black Entertainment Television network.
In 1988, Bob signed with Airborne Records and, with producer Bobby Daniels, crafted his first mainstream album. With a cast of singers and musicians who all had innovative ideas about what being a contemporary Christian meant, Bob Bailey was in-step with albums of the time, like Amy Grant’s Unguarded, Tramaine Hawkins’ The Search is Over and Kathy Troccoli’s Images. The album’s lead single, “Project Girl,” went into regular rotation on the Black Entertainment Television network.
Project Girl
Airborne intended to present Bob as a mainstream R&B artist, filming a video for the album's first single, "Project Girl." The video featured a variety of familiar faces, most notably fellow session singers, Vicki Hampton, Johnny Whittaker and Robin Johnson. https://youtu.be/t7qOxXgYxi4
Airborne intended to present Bob as a mainstream R&B artist, filming a video for the album's first single, "Project Girl." The video featured a variety of familiar faces, most notably fellow session singers, Vicki Hampton, Johnny Whittaker and Robin Johnson. https://youtu.be/t7qOxXgYxi4
Taking The Message To The World
Explaining his transition into the general market, Bob explained to The Tennessean, "I am a gospel singer, but I have to do it in the context of reality. I've taken my music to the streets."
Explaining his transition into the general market, Bob explained to The Tennessean, "I am a gospel singer, but I have to do it in the context of reality. I've taken my music to the streets."
Transition To Session Work
When Airborne Records unexpectedly folded, Bob leaned more heavily into session work, providing background vocals across all genres. Pictured here with Millie Jackson circa 1988 when they worked on her The Tide Is Turning album.
When Airborne Records unexpectedly folded, Bob leaned more heavily into session work, providing background vocals across all genres. Pictured here with Millie Jackson circa 1988 when they worked on her The Tide Is Turning album.
Country Music Calls
As the eighties moved into the nineties, he lent his voice to chart-topping, platinum selling albums like Reba McEntire’s Rumor Has It and For My Broken Heart albums, Dolly Parton’s Home for Christmas, Vince Gill’s I Still Believe in You, Garth Brooks’ Beyond the Season and many more.
As the eighties moved into the nineties, he lent his voice to chart-topping, platinum selling albums like Reba McEntire’s Rumor Has It and For My Broken Heart albums, Dolly Parton’s Home for Christmas, Vince Gill’s I Still Believe in You, Garth Brooks’ Beyond the Season and many more.
Alongside his work in mainstream music...
Bob continued to contribute to contemporary Christian and gospel music. He provided backing vocals on best-selling CCM albums like Rich Mullins’ The World As I Best Remember It Vol. 2, Margaret Becker’s Soul and Sandi Patty’s Find It on the Wings and continued to appear on Christian television. Pictured here with Dr. Bobby Jones & New Life with Vanessa Bell Armstrong on the set of Bobby Jones Gospel.
Bob continued to contribute to contemporary Christian and gospel music. He provided backing vocals on best-selling CCM albums like Rich Mullins’ The World As I Best Remember It Vol. 2, Margaret Becker’s Soul and Sandi Patty’s Find It on the Wings and continued to appear on Christian television. Pictured here with Dr. Bobby Jones & New Life with Vanessa Bell Armstrong on the set of Bobby Jones Gospel.
The Gospel According To Bob Bailey
Throughout the 90s, he featured on projects like the Music City Mass Choir’s We’ve Come to Praise Him, released his own collection, The Gospel According to Bob Bailey, conducted workshops internationally and continued to perform at select church engagements. Watch "No More Pain" https://youtu.be/V4G8ZMs2YJQ
Throughout the 90s, he featured on projects like the Music City Mass Choir’s We’ve Come to Praise Him, released his own collection, The Gospel According to Bob Bailey, conducted workshops internationally and continued to perform at select church engagements. Watch "No More Pain" https://youtu.be/V4G8ZMs2YJQ
Background Singer Candid with Wynonna
After the release of her debut album in 1992, Bob joined Wynonna Judd’s touring cast as a supporting vocalist as she supported the album, a post he would remain in for the next decade. He can be heard on her subsequent releases, Tell Me Why, Revelations, The Other Side, New Day Dawning, The Judds Reunion Live, and What the World Needs Now is Love.
After the release of her debut album in 1992, Bob joined Wynonna Judd’s touring cast as a supporting vocalist as she supported the album, a post he would remain in for the next decade. He can be heard on her subsequent releases, Tell Me Why, Revelations, The Other Side, New Day Dawning, The Judds Reunion Live, and What the World Needs Now is Love.
On Tour With Garth Brooks
In 2014, Bob joined Garth Brooks’ touring cast as a background vocalist, thrilling audiences on tour and in Brooks’ long-standing Las Vegas residency.
WATCH HERE: “Shout” with Garth Brooks
In 2014, Bob joined Garth Brooks’ touring cast as a background vocalist, thrilling audiences on tour and in Brooks’ long-standing Las Vegas residency.
WATCH HERE: “Shout” with Garth Brooks
Imagine
Bob has contributed to Brooks’ recordings since 1992’s Beyond the Season. He joined Brooks and Trisha Yearwood in performance at the funerals of President Jimmy Carter and his wife, Rosalynn. https://youtu.be/SgI-Q9AVvTA?si=e66iTlQDEtXxTGv_
Bob has contributed to Brooks’ recordings since 1992’s Beyond the Season. He joined Brooks and Trisha Yearwood in performance at the funerals of President Jimmy Carter and his wife, Rosalynn. https://youtu.be/SgI-Q9AVvTA?si=e66iTlQDEtXxTGv_
2025
2025 brings the first-ever CD and digital reissue of Bob’s solo discography, as he continues to tour. He is working with filmmaker Odu Adamu on a documentary about his life in music and continues to write and record. He is currently the Vice President (Singers and Recording Artists) of Nashville’s SAG-AFTRA chapter, working behind the scenes on behalf of his peers in the music industry. Bob continues to work as a solo artist with extensive engagement in the international sector, introducing his distinct brand of inspirational music to new audiences in countries like Norway, Denmark, and Sweden.
2025 brings the first-ever CD and digital reissue of Bob’s solo discography, as he continues to tour. He is working with filmmaker Odu Adamu on a documentary about his life in music and continues to write and record. He is currently the Vice President (Singers and Recording Artists) of Nashville’s SAG-AFTRA chapter, working behind the scenes on behalf of his peers in the music industry. Bob continues to work as a solo artist with extensive engagement in the international sector, introducing his distinct brand of inspirational music to new audiences in countries like Norway, Denmark, and Sweden.
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