Feature Photo: Bruce Alan Bennett / Shutterstock.com
Our article on the 10 coolest guitars of all time isn’t a comprehensive history of the guitar—that would be a far more detailed piece than we’re presenting here. Instead, this is a fun look at what we believe are 10 of the coolest-looking guitars in rock and roll history. While “history” is a word we take seriously as a classic rock history site, our focus here is to showcase photos, videos, and stories behind these visually iconic instruments.
Though these guitars are undeniably cool on their own, it was the musicians who played them that truly made them legendary. And, of course, we can’t forget the brilliant minds who designed and built these guitars. The magic happened in the creative partnership between the players and the makers. We hope you enjoy this article, and let us know: what are your favorite-looking guitars?
# 10 – Les Paul – Clunker
Photo: William P. Gottlieb, Public domain, via Wikimedia Commons
Les Paul’s “Clunker” guitar, crafted in 1942, holds a legendary status in the history of electric guitars, representing the pioneering efforts of Les Paul himself — a man who was as much an innovator as he was a virtuoso. The Clunker was Les Paul’s experimental prototype, embodying his early efforts to achieve sustain and volume without the feedback issues that plagued hollow-body guitars. This guitar wasn’t just an instrument; it was a testbed for Paul’s groundbreaking ideas, many of which would shape the future of electric guitar design.
The Clunker began as a heavily modified Epiphone guitar, but Paul transformed it beyond recognition, stuffing it with electronics and experimenting with different materials and configurations to create a solid body that would reduce feedback and enhance sustain. He even cut down and replaced parts of the body, ultimately resulting in an instrument that was far from polished but packed with ingenuity. With this guitar, Paul developed his ideas for multi-track recording, overdubbing, and tape delay, techniques that would later become standard in the music industry.
Les Paul’s dedication to the Clunker and his relentless experimentation led to the eventual creation of the iconic Gibson Les Paul model, which was released in 1952 and went on to become one of the most influential guitars in rock and roll history. The Clunker itself may have been rough around the edges, but it was a turning point in electric guitar design, marking the beginning of a new era in music. Today, it stands as a symbol of Les Paul’s contributions to both guitar-making and music technology, embodying the inventive spirit that would leave an indelible mark on popular music.
Read More: Top 10 Les Paul Songs
# 9 – Stevie Ray Vaughan – Number One
Feature Photo: Jason Lam, CC BY 2.0 <https://creativecommons.org/licenses/by/2.0>, via Wikimedia Commons
Stevie Ray Vaughan’s Fender Stratocaster, famously known as “Number One” or “First Wife,” is one of the most legendary guitars in blues and rock history. Vaughan, a Texas-born guitarist celebrated for his fiery blues style and soulful playing, relied on this guitar throughout his career to craft his signature sound. Number One is a 1963 Fender Stratocaster, though it’s often described as a hybrid since it features parts from other years. Vaughan bought the guitar in 1974 from Ray Hennig’s Heart of Texas Music shop, and it quickly became his favorite instrument, accompanying him on stage and in the studio for the rest of his career.
Number One is easily recognizable by its heavily worn sunburst finish, which shows signs of years of intense playing. The guitar features a thick, V-shaped neck, which Vaughan preferred for its feel and stability, allowing him to apply his famously heavy gauge strings, sometimes as thick as .013s—much heavier than standard strings. This setup, combined with Vaughan’s aggressive playing style, contributed to the Stratocaster’s distinctive, powerful tone, which was perfect for his mix of Texas blues, rock, and jazz influences.
Another iconic feature of Number One is the “SRV” initials Vaughan placed on the pickguard in bold letters, making it instantly identifiable to fans. The guitar also has a left-handed tremolo bridge, which Vaughan left intact despite being right-handed. This unusual setup allowed him to produce unique bends and vibrato effects, adding to his expressive sound.
Vaughan used Number One on almost all of his famous recordings, including classics like “Pride and Joy,” “Texas Flood,” and “Scuttle Buttin’.” His aggressive picking style, combined with the Stratocaster’s bright, biting tone, defined his sound and influenced countless guitarists who followed. After Vaughan’s tragic death in 1990, Number One became a revered piece of rock history, symbolizing the raw energy and passion of Stevie Ray Vaughan’s music. Fender later released a Stevie Ray Vaughan Signature Stratocaster, replicating many of the unique specifications of Number One, allowing fans and musicians to connect with Vaughan’s legacy and his deeply influential blues style.
Read More: Top 10 Stevie Ray Vaughan Songs
# 8 – Jimi Hendrix – Flying V
Feature Photo: Eden, Janine and Jim from New York City, CC BY 2.0 <https://creativecommons.org/licenses/by/2.0>, via Wikimedia Commons
Jimi Hendrix’s Gibson Flying V, famously known as the “Love Drops” guitar, is one of the most iconic instruments in rock history. Hendrix, known for his revolutionary approach to guitar playing and his influential role in shaping the sound of the late 1960s, brought a unique twist to the Flying V, a model already known for its distinctive shape. This particular guitar, crafted in 1967, was custom-painted by Hendrix himself with swirling psychedelic patterns, making it visually synonymous with the spirit of the era. The paint job featured vibrant reds, yellows, greens, and blues in a flowing design, giving the guitar a trippy, eye-catching look that matched Hendrix’s stage persona.
The Flying V quickly became a favorite instrument of Hendrix, especially during his performances in the late 1960s. He used it extensively on his tours, particularly when playing songs that demanded a darker, heavier tone, like “Red House,” a blues standard in his repertoire. Hendrix’s Flying V was equipped with humbucking pickups, providing a rich, powerful sound that cut through his band’s mix and delivered the full, expressive tone he was known for. The guitar’s shape also complemented Hendrix’s left-handed playing style, allowing him to comfortably reach the higher frets and creating a memorable stage image as he performed.
Fans and musicians alike admired Hendrix’s Flying V not only for its distinct look but for the innovation it represented. Hendrix’s fusion of blues, rock, and psychedelia was perfectly complemented by the Flying V’s bold design and powerful sound. After his death, the “Love Drops” Flying V became a cherished relic, symbolizing both Hendrix’s legacy and his creative spirit. The guitar has since been displayed in museums, including the Play It Loud exhibit at the Metropolitan Museum of Art, where it continues to captivate fans and celebrate the lasting impact of Jimi Hendrix on rock music and culture.
Read More: 10 Most Underrated Jimi Hendrix Songs
# 7 – Prince – Cloud
Prince’s Cloud guitar is one of the most iconic instruments in pop music, famous for its unique shape and for its association with the artist’s revolutionary sound and style. Originally designed in the early 1980s, the Cloud guitar was custom-made by Minneapolis-based luthier Dave Rusan for Prince’s film Purple Rain, where it made its debut and became an immediate visual signature for the artist. The guitar’s bold, futuristic look — with its distinctive elongated horn and swirling body — matched Prince’s genre-blurring music and flamboyant stage presence, making it inseparable from his persona.
The Cloud guitar, typically finished in a solid white or sometimes blue, has a sleek, curvy design with gold hardware and stylized fingerboard inlays that contribute to its ethereal aesthetic. It was designed to feel elegant and versatile, fitting seamlessly with Prince’s energetic and theatrical performance style. Over the years, Prince used multiple Cloud guitars in various colors, including yellow, black, and purple, each reflecting different eras of his career and changing aesthetic. These guitars were more than just props; they were fully functional, customized for Prince’s playing style and needs, featuring a single EMG humbucker pickup for a clean but powerful tone that complemented his distinct blend of rock, funk, and pop.
Prince’s Cloud guitar became symbolic of his innovative approach to both music and fashion, blending high musicality with a keen sense of visual artistry. His fans quickly grew to associate the guitar’s shape with his on-stage energy, and it became a sought-after piece of memorabilia. Over the years, replicas of the Cloud guitar have been produced by Schecter and other manufacturers, allowing fans and musicians to own a piece of the icon’s legacy. Today, the Cloud guitar remains a symbol of Prince’s boundary-pushing spirit, both in music and in personal expression, and is widely celebrated as one of the most distinctive guitars in music history.
Read More: 10 Most Rocking Prince Songs
# 6 – Zakk Wylde – The Grail
Feature Photo: TDC Photography / Shutterstock.com
Zakk Wylde’s guitar known as “The Grail” is one of the most recognizable instruments in rock and metal, reflecting both his signature sound and his connection to the legendary guitarist Randy Rhoads. The Grail is a Gibson Les Paul Custom with Wylde’s iconic black-and-white bullseye design, which has become as much a symbol of his style as his fiery, aggressive playing. Wylde received the guitar early in his career, just before joining Ozzy Osbourne’s band in the late 1980s, and it quickly became his go-to instrument for both recording and live performances.
The bullseye design, now inseparably associated with Wylde, came about by accident. Originally, Wylde had requested a pattern similar to Rhoads’ polka-dot guitar as a tribute to the late guitarist, but when the design came out looking more like a bullseye, he decided to keep it. The striking pattern, combined with the classic Les Paul shape, made The Grail instantly recognizable on stage and in photos. Over time, it became a visual representation of Wylde’s brand of heavy, powerful riffs and blazing solos.
The Grail’s sound is a perfect match for Wylde’s aggressive, hard-hitting playing style. Equipped with EMG 81/85 active pickups, it delivers a high-output, heavy tone that cuts through the mix with clarity and punch, ideal for Wylde’s signature mix of pinch harmonics, rapid-fire picking, and thick, sustaining notes. Wylde used The Grail extensively throughout his career with Ozzy Osbourne, on songs like “No More Tears” and “Mama, I’m Coming Home,” as well as with his own band, Black Label Society, where it continued to define his sound.
Wylde’s connection to The Grail goes beyond just its functionality as a guitar; it’s a part of his musical identity. Fans and fellow musicians alike recognize it as an integral element of his persona, symbolizing his dedication to the raw energy and power of rock and metal. Over the years, The Grail has sustained its share of wear and tear, but Wylde continues to play it, reinforcing its status as a beloved, battle-worn instrument. In addition, Gibson and Wylde collaborated to release signature models, bringing The Grail’s iconic design and formidable sound to fans worldwide, and ensuring that this piece of metal history lives on for future generations.
Read More: Top 10 Black Label Society Songs
# 5 – B.B. King – Lucille
Feature Photo: Nina Alizada / Shutterstock.com
B.B. King’s iconic guitar, affectionately named “Lucille,” is as legendary as the bluesman himself, carrying a story and legacy that resonate far beyond its strings. The name “Lucille” originated in 1949, when King was playing in a small club in Twist, Arkansas. During his performance, a fight broke out between two men, causing a kerosene barrel used for heat to tip over and start a fire. Everyone evacuated, but King, realizing he had left his guitar inside, risked his life to run back and retrieve it. Later, he learned that the fight was over a woman named Lucille. From that day on, he named his guitar “Lucille” as a reminder never to fight over a woman or do anything as foolish as running into a burning building.
King’s “Lucille” was not a single guitar but rather a series of Gibson guitars that he named over the years, most famously the Gibson ES-355. Gibson produced various models specifically tailored to King’s preferences, including removing the F-holes from the body to reduce feedback—a significant innovation for electric blues musicians of the time. Lucille’s signature sound combined the rich, warm tones of the semi-hollow body with King’s unparalleled vibrato technique, which gave his playing its distinctive “crying” sound. King’s style, known for its expressive bending and vibrato, became inseparable from Lucille’s voice, allowing him to tell stories and convey deep emotion through his music.
In 1980, Gibson honored B.B. King by releasing a custom model known as the Gibson B.B. King “Lucille,” based on his specifications. The guitar featured a sleek ebony finish, a maple neck, and, uniquely, a semi-hollow design without F-holes to reduce feedback. King’s relationship with Lucille spanned decades, and he used her to create some of his most famous recordings, including classics like “The Thrill is Gone” and “Sweet Little Angel.”
Read More: Top 10 B.B. King Songs
# 4 – Jerry Garcia – Tiger
Photo: Grateful Dead, CC BY-SA 3.0 <http://creativecommons.org/licenses/by-sa/3.0/>, via Wikimedia Commons
Jerry Garcia’s custom guitar, “Tiger,” is one of the most famous and revered instruments in rock history, crafted specifically for him by master luthier Doug Irwin. Built in 1979 and played by Garcia through over a thousand Grateful Dead concerts until 1989, Tiger became a defining part of his sound and style, embodying his eclectic influences and technical prowess. Known for its intricate inlays, custom electronics, and rich tonal capabilities, “Tiger” wasn’t just an instrument for Garcia; it was an extension of his musical spirit and improvisational genius.
Doug Irwin built Tiger with a combination of exotic woods and meticulous craftsmanship. The body is primarily constructed from cocobolo, a Central American hardwood known for its vibrant tone and striking appearance. This dense wood gave Tiger a unique resonance and sustain that complemented Garcia’s playing style. The guitar features a maple core sandwiched between the cocobolo top and back, resulting in a rich, full-bodied sound. It also has a neck made of five layers of purpleheart and maple, adding both strength and beauty to the instrument. Tiger’s distinctive inlay work, including the tiger image near the bridge, reflects Irwin’s attention to detail and Garcia’s love for unique artistry.
What truly set Tiger apart were its custom electronics, which allowed Garcia unparalleled control over his tone. It was equipped with DiMarzio humbucking pickups—one SDS-1 single-coil in the middle and two Super IIs at the neck and bridge—that gave Garcia a range of tonal options. Tiger also featured an onboard effects loop, which allowed Garcia to control external effects directly from the guitar without compromising signal clarity. This setup gave him the flexibility to seamlessly transition through different tones during his extended improvisations, making it perfect for the Grateful Dead’s famously exploratory live performances.
Tiger’s impact on fans and fellow musicians was profound, becoming an iconic part of Garcia’s image. The guitar’s distinctive look and sound captured Garcia’s innovative approach to music and his willingness to push boundaries. After Garcia’s death in 1995, the guitar became the center of a legal dispute but was ultimately returned to Doug Irwin, who sold it at auction in 2002 for nearly $1 million.
Read More: 10 Essential Jerry Garcia Songs That Defined His Solo Career
# 3 – Bo Diddley – Cigar Box
Feature Photo: Masao Nakagami, CC BY-SA 2.0 <https://creativecommons.org/licenses/by-sa/2.0>, via Wikimedia Commons
Bo Diddley was a musical innovator who helped shape the sound of early rock and rhythm and blues. His unique cigar box guitar was an extension of his personality—bold, unconventional, and deeply rooted in blues tradition.
The cigar box guitar itself was crafted by Diddley in the 1950s. He wanted an instrument that stood out visually as much as it did sonically. Instead of using the standard guitar shape, he opted for a rectangular body that resembled a cigar box, giving the instrument its nickname. This unusual shape and design were inspired by the makeshift guitars that blues musicians would create from cigar boxes, broomsticks, and wire—tools often used by musicians with limited resources in the rural South. Diddley’s choice to adopt this design connected him to a lineage of blues musicians, while also giving his instrument a modern, rock-and-roll edge.
Diddley’s cigar box guitar wasn’t just a gimmick; it was a carefully crafted tool that allowed him to achieve a unique tone and visual presence. The rectangular shape amplified his powerful stage presence and complemented his innovative playing style. When Bo Diddley took the stage with his homemade guitar, it became an instant part of his identity, fascinating audiences and inspiring musicians worldwide. He would play this guitar on iconic songs such as “Bo Diddley” and “Who Do You Love,” cementing his signature beat and percussive playing style.
Bo Diddley’s cigar box guitar remains one of the most iconic instruments in rock history, symbolizing the spirit of innovation and resourcefulness that defined his music. The guitar, much like Diddley himself, broke the mold and inspired countless musicians to experiment with their sound and style. It has also sparked a resurgence in cigar box guitar building, with musicians and luthiers alike paying homage to Diddley’s legacy by creating their own versions of this distinctive instrument.
Read More: Top 10 Bo Diddley Songs
# 2 – Eddie Van Halen – Frankenstrat
Feature Photo: RobinStrower / Shutterstock.com
Eddie Van Halen’s Frankenstrat is a groundbreaking guitar that not only defined his sound but also became one of the most iconic instruments in rock history. Born out of Eddie’s desire to combine the best aspects of a Gibson and a Fender, the Frankenstrat was his attempt to create a guitar that could deliver the thick, powerful tones of a Gibson with the sleek playability of a Fender Stratocaster. Dissatisfied with what was commercially available, Eddie took matters into his own hands, crafting a guitar that would allow him the versatility and power he needed to revolutionize guitar playing.
Eddie began by purchasing a factory-second Strat-style body for around $50 and added a maple neck. He then installed a Gibson PAF humbucker in the bridge position to get the beefy, aggressive tone he wanted, though he had to chisel out the body himself to make it fit. Using his own inventive approach, Eddie shielded the guitar’s electronics with aluminum foil and wired it with a single volume knob labeled humorously as “Tone.” The tremolo bridge was left partially unfastened, allowing for the dramatic “dive bomb” effects that became a hallmark of his playing. He also added a quarter (dated 1971) near the bridge to keep the tremolo arm in place, a signature touch that fans grew to recognize.
Visually, Eddie spray-painted the guitar himself in black and white stripes, later adding the now-iconic red layer in the early ’80s. This DIY aesthetic became synonymous with Eddie’s innovative and rebellious style. The guitar wasn’t just a tool; it was a statement piece that set him apart visually and sonically. Fans and fellow musicians alike were captivated by the Frankenstrat, not only because of its unconventional appearance but because it embodied Eddie’s willingness to push boundaries and experiment.
The Frankenstrat became famous on stages worldwide, especially in performances of “Eruption,” “Panama,” and other Van Halen classics. Its influence extended beyond Eddie’s own performances; the Frankenstrat inspired a generation of guitarists and builders, leading to the creation of the “superstrat” style—a high-performance, heavily modified guitar aimed at rock and metal players. To this day, the Frankenstrat symbolizes Eddie Van Halen’s creative genius and relentless pursuit of innovation, forever changing the way guitars are built, played, and admired in the rock world.
Read More: Van Halen’s Best Song On Each Of Their Studio Albums
# 1 – Jimmy Page – Gibson EDS-1275
Feature Photo: Bruce Alan Bennett / Shutterstock.com
Now you know this just had to be number one. I remember as a kid seeing Jimmy Page play this at Madison Square Garden in 1977 and being just completely blown away by just how cool this was. Between that guitar and that white outfit with the rose, I was staring at a rock and roll God. Jimmy Page’s iconic Gibson EDS-1275 guitar is one of rock history’s most distinctive instruments, known for its double-neck design and association with some of Led Zeppelin’s most legendary live performances. The story behind this unique guitar dates back to 1971, when Page sought a solution to a logistical challenge presented by Stairway to Heaven, Led Zeppelin’s epic anthem from Led Zeppelin IV. The song required both a six-string and a twelve-string guitar to capture its acoustic and electric sections in a single performance, so Page turned to Gibson’s EDS-1275 to seamlessly transition between the two sounds.
The EDS-1275 guitar, which features one six-string and one twelve-string neck, was originally released by Gibson in the early 1960s. Although it wasn’t initially a major hit, its unique design found appeal among certain musicians, and Page’s choice of the EDS-1275 cemented its legendary status. Known as the “SG Double Neck” because of its resemblance to the Gibson SG, the guitar featured in performances of “Stairway to Heaven” and other Led Zeppelin tracks requiring multiple tunings and varied sounds, including “The Song Remains the Same” and “The Rain Song.”
Page’s use of the EDS-1275, however, wasn’t limited to its practical benefits; it became a powerful visual symbol, amplifying Led Zeppelin’s mystique. Custom-built for Page in a striking cherry red finish, this particular guitar contributed to his signature style. The instrument has since become a highly sought-after collector’s item, and Gibson has reissued it in tribute to Page’s influence. The EDS-1275 remains one of the most iconic guitars in rock history, symbolizing Page’s innovative approach to live performance and his dedication to creating an unforgettable sound and visual experience.
Read More: Top 20 Jimmy Page Guitar Solos
10 Of The Coolest Looking Guitars In Rock Historyarticle published on Classic RockHistory.com© 2024
