Bo Diddley被认为是50年代最有弹性的吉他节奏家，同时也是个技术熟练的木匠。在他的音乐里，很早的就加入了大量非传统的节拍，是位具有影响力的早期摇滚乐手，后来的很多摇滚乐手都或多或少的受到了他音乐风格的影响。
 
Bo Diddley的畅销单曲不多，但是他的特点非常独特，以下是一位著名乐手对Diddley的评论：“Bo Diddley的音乐是庞大的，满含着非洲粗野而又性感的力量，但总能深深地打动听者。在他的声音中，你能听到一切神秘的事物。他演奏着真正简单的东西，却带着令人难以置信的权威。他就像只公牛；他拥有公牛的性格。他的音乐让我想到Muddy Waters的布鲁斯，不同的是，Bo Diddley将这种音乐带到城镇之中，让人们随之摇摆。他的嗓门很大，但他的叫喊不止大声，而且深沉。”
 
Diddley的手很长，从手腕到指尖有将近一英尺，所以他在真正意义上控制着他的吉他。他自己利用木匠技术制作了一把独特的方形吉他，这就是后来Gretsch牌吉他。
 
He only had a few hits in the 1950s and early 60s, but as Bo Diddley sang, You Cant Judge a Book by Its Cover. You cant judge an artist by his chart success, either, and Diddley produced greater and more influential music than all but a handful of the best early rockers. The Bo Diddley beat — bomp, ba-bomp-bomp, bomp-bomp — is one of rock & rolls bedrock rhythms, showing up in the work of Buddy Holly, the Rolling Stones, and even pop-garage knock-offs like the Strangeloves 1965 hit I Want Candy. Diddleys hypnotic rhythmic attack and declamatory, boasting vocals stretched back as far as Africa for their roots, and looked as far into the future as rap. His trademark otherworldly vibrating, fuzzy guitar style did much to expand the instruments power and range. But even more important, Bos bounce was fun and irresistibly rocking, with a wisecracking, jiving tone that epitomized rock & roll at its most humorously outlandish and freewheeling.
 
Before taking up blues and R&B, Diddley had actually studied classical violin, but shifted gears after hearing John Lee Hooker. In the early 50s, he began playing with his longtime partner, maraca player Jerome Green, to get what Bos called that freight train sound. Billy Boy Arnold, a fine blues harmonica player and singer in his own right, was also playing with Diddley when the guitarist got a deal with Chess in the mid-50s (after being turned down by rival Chicago label Vee-Jay). His very first single, Bo Diddley/Im a Man (1955), was a double-sided monster. The A-side was soaked with futuristic waves of tremolo guitar, set to an ageless nursery rhyme; the flip was a bump-and-grind, harmonica-driven shuffle, based around a devastating blues riff. But the result was not exactly blues, or even straight R&B, but a new kind of guitar-based rock & roll, soaked in the blues and R&B, but owing allegiance to neither.
 
Diddley was never a top seller on the order of his Chess rival Chuck Berry, but over the next half-dozen or so years, hed produce a catalog of classics that rival Berrys in quality. You Dont Love Me, Diddley Daddy, Pretty Thing, Diddy Wah Diddy, Who Do You Love?, Mona, Road Runner, You Cant Judge a Book by Its Cover — all are stone-cold standards of early, riff-driven rock & roll at its funkiest. Oddly enough, his only Top 20 pop hit was an atypical, absurd back-and-forth rap between him and Jerome Green, Say Man, that came about almost by accident as the pair were fooling around in the studio.
 
As a live performer, Diddley was galvanizing, using his trademark square guitars and distorted amplification to produce new sounds that anticipated the innovations of 60s guitarists like Jimi Hendrix. In Great Britain, he was revered as a giant on the order of Chuck Berry and Muddy Waters. The Rolling Stones in particular borrowed a lot from Bos rhythms and attitude in their early days, although they only officially covered a couple of his tunes, Mona and Im Alright. Other British R&B groups like the Yardbirds, Animals, and Pretty Things also covered Diddley standards in their early days. Buddy Holly covered Bo Diddley and used a modified Bo Diddley beat on Not Fade Away; when the Stones gave the song the full-on Bo treatment (complete with shaking maracas), the result was their first big British hit.
 
The British Invasion helped increase the publics awareness of Diddleys importance, and ever since then hes been a popular live act. Sadly, though, his career as a recording artist — in commercial and artistic terms — was over by the time the Beatles and Stones hit America. Hed record with ongoing and declining frequency, but after 1963, hed never write or record any original material on par with his early classics. Whether hed spent his muse, or just felt he could coast on his laurels, is hard to say. But he remains a vital part of the collective rock & roll consciousness, occasionally reaching wider visibility via a 1979 tour with the Clash, a cameo role in the film Trading Places, a late-80s tour with Ronnie Wood, and a 1989 television commercial for sports shoes with star athlete Bo Jackson.