He is known for his position in the band "The Yarbs" (bandleader Chris Pestalozzi) which played cover songs, standards, and originals, crossing many genres, with an emphasis on original compositions and Blues. In 1968, Radcliff also joined "The Northside Blues Band", alongside Brett Littlehales (harmonica), Guy Dorsey (keyboard), William Bowman (bass), and Van Holmead (drums).
Radcliff's spectrum of musical inspirations expanded as he continued to explore different artists. He was particularly inspired by the Butterfield Blues Band (Paul Butterfield, Mike Bloomfield, and Elvin Bishop), but also drew from country guitarist James Burton (from Ricky Nelson's band), Kenneth "Thumbs" Carllile (from Jimmy Dickens band), Don Rich (from Buck Owen's Band), Steve Cropper, Slim Harpo, Howlin' Wolf, Muddy Waters, The Ventures and many others. He was also influenced by the Rolling Stones, Eric Clapton and many other British Blues Bands. Radcliff met many blues musicians during this period, such as Freddy King and Buddy Guy (1968).
A seminal moment in Radcliff's musical development came when he attended the Ann Arbor Blues Festival in 1969. Not only did he meet Dick Watermen, who became a friend, but he also saw Magic Sam live for the first time. Sam's Chicago West Side Blues sound captivated Radcliff as it was unlike anything he'd ever heard. This performance inspired Radcliff to form his own band – a trio he modeled after Sam's band. Radcliff was so inspired by Magic Sam that he soon boarded a bus to Chicago, venturing to meet his newfound guitar idol. Radcliff arrived in Chicago only to learn Magic Sam had suffered a major heart attack and was in Cook County Hospital. Radcliff sat by his bedside until Sam woke up. He explained that he had seen him at the Ann Arbor Festival and Sam was receptive to young Radcliff's pilgrimage to meet him.
After Sam recovered, he invited Radcliff back to his home at 1513 South Harding Street, in the heart of Chicago's West Side. Sam introduced Radcliff to the West Side Chicago Blues scene at such venues as The Alex Club (1815 Roosevelt Road) and the L & A Lounge on Pulaski (where Sam was a part-time bartender when he couldn't get enough work as a musician). They also went to The Key Largo where Otis Rush often performed and The Flash Lounge where Sam introduced Radcliff to Eddie Clearwater.
Some of the other musicians that Sam introduced Radcliff to in Chicago included: Mighty Joe Young (guitar), Ernie Gatewood (who also sometimes played bass for Magic Sam), Otis Rush, Jimmy Dawkins, Mac Thompson (bass), and Letha Jones (pianist Johnny Jones widow) and many other musicians. Radcliff often witnessed Sam performing with the above-mentioned musicians and many others.
Over the next six months, Radcliff visited Sam a number of times – staying with Sam's family in Chicago. One of the most important messages that Sam gave to Radcliff was to listen to all kinds of music (country, jazz, pop, classics etc..) and to continue to be broadminded about the music he listened to because developing 'your own style' was important, along with continuing to grow as a musician. Sam died in December 1969 at age 32 – from a heart attack. Radcliff and Dick Waterman attended Sam's funeral together.
By this time, Radcliff's style was infused with Magic Sam's unique sound. However, the breadth of Radcliff's music drew no boundaries his own stylistic voice emerged, helping his career blossom. Writer Dave Hussong Vintage Guitar Magazine (1990) touches on Radcliff's expansive musical range as a vocalist, instrumentalist, and live performer:
"Unencumbered by style restrictions, Radcliff brings a sense of intensity and conviction, both instrumentally and vocally (the latter being an area where many 90's interpreters fall face down) that puts his, and this, live performance into a very special league of its own."
In the early 1970s, he began performing with his own band at clubs in the Washington D.C. area with a few key residencies: He performed a few nights each week at Cousin Nicks, and Sundays and Monday's at Top 'o Foolery Jazz Club. He also frequently performed at Mr. Henry's and The Childe Harold. Radcliff recorded his first 45 RPM single in 1974 on Aladdin Records with "It's Been a Long Long Day" by Amos Milburn and the B-side was "That's All I Need" which he learned from Magic Sam.
Members of his band during this time included many of the great Washington DC players; Steve Shaw, Victor Spano, Dave Walker, Dick Heintze, Robbie Magruder, Joe Bradley, TNT Tribble, Tom Slavin, and Danny Gatton.
In 1977, he relocated to New York where he took a day job in a bookstore. At night, he was an integral musician as part of the thriving New York music club scene. He performed most evenings and was one of the house musicians at the Lone Star Cafe and at Tramps, working with Kinky Friedman, Bernard Purdie, Otis Rush, Lowell Folson, and Big Jay McNeeley, amongst many others. Radcliff's own band played at many clubs, including CBGBs. Radcliff's band was one of the few Blues bands playing there as his songwriting and style continued to flourish.
During this time, there were many chance meetings at his shows, including when John Belushi saw Radcliff play at the Lone Star Café with Kinky Friedman in the late 1970s. John then recruited Radcliff for guitar lessons. During this time, he regularly saw Belushi. Subsequently, Belushi invited Radcliff to perform in the very first Blues Brother's show, featuring Belushi and Roomful Of Blues.
Radcliff's career continued to heat up and in 1984 he recorded "Early In the Morning", his first 33 RPM album, and by 1987 he began recording and performing full-time. Between 1989- and 1998, Radcliff released five albums on the Black Top Record label: "Dresses Too Short", "Universal Blues", "There's A Cold Grave In Your Way", "Live At The Rynborn" and "Live At Tipitina's." He toured extensively all over the world, performing at many premiere American and European festivals including the Berlin Jazz Festival, The Peer Festival in Belgium, The Byron Bay Blues Festival in Australia, the Warrnambool Festival in Australia, the Harvest Blues Festival in Ireland, the Lugano Blues Festival in Switzerland, the Lucerne Blues Festival in Switzerland, the Malmitalo Festival in Finland, The Aguas Blues Festival in Aguascalieutes Mexico, the Granada Jazz and Blues Festival in Spain, the San Remo Blues Festival in Italy, and the Café Volga Festival in Japan. Radcliff performed at many other festivals, including tours with Earl King where Radcliff played under his own name and also as Earl's backing band.
In addition to the above-mentioned festivals, Radcliff toured Europe and the United States extensively with the "Blacktop Artists Tours" that included Robert Ward, Snooks Eaglin, Ronnie Earl, Anson Funderburgh, Clarence Holliman, and James "Thunderbird" Davis. In 1990, Radcliff received a New York Music Award from K-Rock radio station for "Best Blues Artist". That year, he also received a five star review from the October issue of Downbeat Magazine for "Dresses Too Short." From Downbeat Magazine:
"The firebrand's Fender shudders, diters, and fulminates in a rough, deep-seated kind of ecstasy too seldom encountered in this age of superficial, smoke and verbiage blues guitar. Fitting the templates of order and creative intelligence over his crowded bursts of simultaneous leads, bass lines, and chords, the Washington D.C. native indulges his passion for Buddy Guy and Magic Sam without aping the greats. Moreover, Radcliff works up a true sweat inspiriting verse behind a stealthily incisive, stirring voice that's roughly a cross between Magic Sam's and Jimmy Johnson's."
Guitar Player 's April 1990 issue does an extensive interview of Radcliff, praising his style, and "Dresses Too Short" on many levels:
"The Black Top album runs an A-to-Z gamut of blues styles before closing with "Kool And The Gang," an early single from the group by the same name, with Radcliff's guitar impersonating the entire horn section, choreography and all…..."
Downbeat Magazine from October 1990 also gave a stellar review of "Dresses Too Short":
"By dint of his powers, he elevates good songs…to the point where the entire program screams out for repeated plays. Let's just say "Dresses Too Short" provides the jolt of a bungee jump off the 59th St. Bridge."
His "Live at the Rynborn" record showcases his brilliance as a live performer. Like a chameleon, Radcliff's selections on this record span musical time and genres. It was recorded at the now defunct "Rynborn" club in New Hampshire which helped spawn his following in that area. Radcliff continues to perform in New Hampshire at Nelson's Candy Store – yearly – and sells out every time. Steve Hoffman, DJ from "The Blues Experience" on WDCU-FM from Washington D.C. had some choice words about Radcliff's playing on the "Live at the Rynborn".
"While many guitarists get into a call-and-response pattern with the band or the singer, Bobby is his own one-man call-and-response machine. He juxtaposes guitar rhythm and lead parts so abruptly, it's like a raging battle….He'll motor along with a standard blues shuffle and then suddenly, approaching a curve, slam on the accelerator and careen, screeching, into his own freaky, staccato Funksville….Bobby doesn't just perform the blues. He's possessed by them. He plays so angry and sings so hurt, it's like a catharsis – maybe even an exorcism – for both him and his audience. When I see or hear Bobby, I don't feel much like dancing, despite his exhortation early on this live recording. I'd rather sit back, close my eyes, and let his playing zap my central nervous system like some sort of musical electroshock therapy…"
In 1991, Radcliff underwent two hand surgeries from which he made a full recovery and continued touring and playing at festivals. His 1991 release, "Universal Blues" illustrated his continuous versatility and increasing talent, as described by Dick Shurman: "As Bobby typifies in the hands of a virtuoso who can defy the apparent limits of two hands and one guitar, the juggled parts interweave deftly, punctuating snarling, squalling, grinding bends with relentless drive."
In 2005 Radcliff released "Natural Ball" with producer Bill Bowman on the Rollo Label. Like all his records, it was released to critical acclaim. Here's what the July 2005 issue of Blues Revue Magazine had to say:
"Radcliff, one of the most under-recognized players on the scene, is a phenomenally gifted musician whose soulful delivery, funky picking, and sparse, stinging West Side sound (as personified by his hero, Magic Sam) is distinctive and electrifying…..Switching from lead to rhythm faster than you can say Freddie King…..Radcliff's style is so personalized that he even makes over-recorded material such as "Catfish Blues" his own; his John Lee Hooker moaning and clipped, taut, effects-free guitar lines burn with vicious fluidity."Radcliff subsequently recorded "Freaking Me Out" (Krellno Records) – released in 2011 - which was his first all originals CD. This CD, produced by Chris Matheos (who is also the bassist on this record) also features Radcliff's original artwork on the front cover and inside.
Here's what Blue Review Magazine writer Thomas J. Cullen III said about "Freaking Me Out" (July/August Issue, 2011)
"The latest album from the NYC-based guitarist/vocalist is his first in seven years and the first filled with all original material. One of the chief exponents of the West Side sound. Although he grew up in Washington DC, Radcliff was mentored in Chicago by Magic Sam, one of the few living guitarists who can make that claim. I was fortunate to see Magic Sam live, and I've seen Radcliff live a number of times, most recently in NYC in March of this year. I can say without hesitation that he is the closest guitarist to Magic Sam I've ever heard."
His new CD (June 2016) "Absolute Hell" is another record of all originals produced by Chris Matheos and Radcliff. He builds on the music that has served him well and stretches it into new directions. With slivers of reggae, punk, humor, and darkness (the title is – after all, "Absolute Hell") it is a melting pot of songs – lyrical and instrumentals – that will underscore Radcliff's continuation as a vital musician on the scene today. "Absolute Hell" and "Freaking Me Out" are each rounded out by Radcliff's paintings which grace the cover.
Other interesting facts about Radcliff include his time spent with Jimi Hendrix in August 1967 - during the week when "Are You Experienced" was initially released in the United States. Radcliff was 15 years old and borrowed his mother's car to drive Hendrix to his shows at the Ambassador Theater at 18th and Columbia in Washington, D.C., and then to parties that followed each performance that week. Radcliff said the first shows were nearly empty, but once the record hit, they were packed. He remembered that Hendrix consistently played with the same passion and intensity each night – whether there were only a few people in the audience – or the theater was at capacity.
Radcliff is considered an authority on Magic Sam, and continues to carry on that West Side Chicago Blues style, but is widely acknowledged as a true original with his sound. He plays many styles on acoustic guitar – with his trio – but is often seen playing his signature Gibson Les Paul. He remains an active bandleader and in-demand guitarist and singer. He continues his steady monthly residency at Terra Blues in New York City – which began in 1994. In addition, he performs throughout the United States and Europe. In 2015 he was inducted into the New York Blues Hall of Fame as a Master Blues Artist. He has recently guested with: Al Copley's Roomful of Blues Reunion Band, The Nighthawks, Bob Margolin's All Star Band, Jimmy 'Fast Fingers' Dawkins, Mark Hummel & Rusty Zinn, Byther Smith, Bruce Ewan, and most recently on Blues Violinist and singer/songwriter Ilana Katz Katz's record "Movin' On.'" (2016).
Early in the Morning (A-Okay, 1985)
Dresses Too Short (Black Top, 1989)
Universal Blues (Black Top, 1991)
There's a Cold Grave in Your Way (Black Top 1994)
Live at the Rynborn (Black Top 1997)
Natural Ball (Rollo Records, 2004)
Freaking Me Out (Krellno Records 2011)
Absolute Hell (Krellno Records 2016)
Blues Cocktail Party Blacktop, 2009)
Blues Pajama Party (Blacktop Records) 1992
She's Lightning When She Smiles (Dave Soldier: Robi Droli / Newtone, 1994)
Traveling Fool (Brad Vickers and his Vestapolitans: Man Hat Tone, 2011)
Stuck With The Blues (Brad Vickers and his Vestapolitans: Man Hat Tone, 2012)
Movin' On (Ilana Katz Katz: Regina Royale, 2016)