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My 5 Favorite Jazz Solos of All Time

My 5 Favorite Jazz Solos of All Time

What is freedom in music? Is that even a thing? We all want to express ourselves effectively when playing our instruments, and we all want to play beautiful melodic jazz solos. But what exactly does that freedom of expression mean. Doesn’t it mean something different to each of us?

If there’s one music genre that has always been synonymous with freedom and unfiltered expression of oneself, it’s Jazz. When playing a Jazz tune, you only have to follow a general song structure. It could be as simple as a Blues form, where you have only twelve bars played repeatedly.

Even a more complicated Jazz Standard only has a few different sections (A section, B section). Once you know the structure, you have nothing else to learn.

You can improvise over these songs freely. You can even change the chords if you know what you’re doing. This approach defines the Jazz mindset, and this is what “freedom in music” means to me.

Now, how do you learn to play with the Jazz mindset? Well, Jazz is a language, and so is music in general. Do you remember how you learned to speak English (or your mother tongue)?

You learned by imitating your parents or the people you had around when you couldn’t talk. If music and improvisation are languages, the process should be the same. Listen, imitate, and repeat.

My Five Favorite Jazz Solos

These excellent improvised performances helped me sculpt my style of improvisation in music with the Jazz mindset, so don’t think you’re going to sound like a copy of somebody else if you decide to learn other people’s solos. You will sound like the sum of your influences, precisely like you do when talking.

Wes Montgomery – Tune Up (from 0:25 to 2:25)

Wes Montgomery embodies the spirit of Jazz guitar. He was a fantastic example of musicality, improvisational ability, and technical mastery of the instrument. Montgomery had a unique physical approach to playing the guitar. He famously played with his thumb instead of a pick.

This peculiarity was a massive determining factor in his sound, but you might be interested in knowing that it wasn’t a choice determined by tone preferences.

Back in the 40s, when Wes was learning how to play the guitar, he worked as a machinist throughout the day, so he could only practice late at night. He adopted his famous thumb technique because he didn’t want to annoy his neighbors by playing too loud.

Like almost all early Jazz musicians, Montgomery thought that the only way to learn music was through imitation. That’s probably why when he bought his first guitar in 1943, after hearing a Charlie Christian record for the first time, he spent the better part of his first year as a guitar player trying to copy Christian note by note.

Wes Montgomery Jazz Solo

This Jazz standard “Tune-Up” version is from the 1963 album Fusion! Wes Montgomery with Strings. The jazz guitarist from Indianapolis performs, in my opinion, one of his most excellent solos in this song, which is also a quintessential representation of his overall guitar playing style.

Wes had the habit of starting his improvisations with single-note lines, only to move to octaves and block chords later, closer to the solo’s climax.

This solo-development technique displays a very clever improvisational approach based on using the natural strengths of the guitar to your advantage.

Dynamic differences are an essential part of playing good-sounding solos, and Wes knew he needed to start low and gradually go higher in intensity. He achieved this by making his guitar sound like more than just one instrument using octaves, one of his signature moves.

What are octaves? Picture yourself playing a C note located at the 5th fret of the G string. You can add another C note, either an octave higher (8th fret of the high E string) or lower (3rd fret of the A string) to create a bigger, fuller sound.

You’re only playing a doubled C note at the end of the day, but this is like having an inbuilt octave pedal or another guitarist playing the added note in sync with you.

So, you’re essentially doubling yourself. Wes could do this fluently, and he was able to play high-speed lines that most guitarists would struggle to play in a single-note style, let alone with octaves.

In this solo, Wes Montgomery proves that you don’t necessarily need to have received formal training in music to understand harmony and Jazz soloing deeply. He couldn’t read music as well. Remember, music is a language, and like you should learn how to talk before you know how to read, you can expect that the same concept will apply to music.

  • Wes Montgomery – Guitar
  • Milt Hilton – Bass
  • Kenny Burrell – Guitar
  • Hank Jones – Piano
  • Osie Johnson – Drums
  • Jimmy Jones – Conductor, Arranger

“Regardless of what you play, the biggest thing is keeping the feel going.” – Wes Montgomery

John Scofield – Alone Together (from 0:55 to 2:05)

John Scofield is, without a doubt, one of the greatest Jazz guitar players alive today. The wide variety of his perceivable influences resulted in his unbelievably unique style. Like most guitar players of his time, Scofield started playing guitar after being influenced by the British Invasion.

Still, when he went to the famous Berklee College of Music in Boston during the early 70s, “Sco” wanted to become a Jazz guitarist, playing only straight-ahead Jazz.

When he left Berklee, the music genre known as Jazz-Fusion was beginning to become popular, and jazz-influenced guitar players were expected to play with a Rock-Blues attitude. So, when Jazz-Funk drummer Billy Cobham called him to join his band in 1975, he had to develop his style further, mixing the earlier Rock and Blues influences with the Jazz approach and vocabulary he had acquired at Berklee.

The result was a slightly overdriven bluesy guitar tone used to play bebop lines. Still, although accurate, this definition doesn’t do justice to the uniqueness of Scofield’s playing style, which is hard to define.

The peculiarities in Scofield’s playing must have intrigued even the legendary Jazz trumpet player Miles Davis because he called Sco to join his electric band in 1982.

John Scofield jazz solo

In this “Alone Together” performance, we can admire the wonderful time feel that John Scofield has over a swing groove, which goes to show the love that Sco has for straight-ahead traditional Jazz. Still, his modern note choices enrich this relatively traditional “laid-back” way to interpret the swing feel.

Scofield can deal with improvising over chord changes like a bebop player, a rock-blues guy, or a contemporary jazz guitarist, all at once. Anyway, independently of the approach he chooses, he’s always able to glue everything together and perform coherent Jazz improvised solos.

The sporadic use of octaves and block chords throughout the entire length of this solo makes us notice Wes Montgomery’s influence on John Scofield.

At the same time, we can find the modern elements of his improvisational style in the use of open strings used as extensions within chords and during the faster phrase that he plays during the B section of the song.

Overall, this is a beautiful solo, played by one of the most personal-sounding jazz players to have ever lived, and it will help you understand what it means to play Jazz on guitar.

  • John Scofield – Guitar
  • Chris Minh Doky – Double Bass

“Hang on to your eccentricities because they will give you a style.” – John Scofield

Clifford Brown – September Song (from 2:35 to 3:50)

When in 1956, Clifford Brown tragically died at the young age of 25 in a car accident, the Jazz world lost one of the purest and most promising talents ever to play the trumpet.

By the time Clifford Brown turned 25, he had already composed and recorded ten albums as a bandleader (or co-leader), having gifted the world with three pieces that later became Jazz standards that other musicians play over even nowadays.

The tunes “Joy Spring”, “Daahoud”, and “Sandu” are part of the repertoire of most Jazz musicians all over the world.

The performances he was able to deliver on his recordings are unbelievably excellent and mature for a musician in his early twenties, which makes you wonder about what Brown could have achieved hadn’t he been in that unfortunate car accident.

The three albums that Clifford Brown recorded with drummer Max Roach as part of the Clifford Brown and Max Roach Quintet are milestones in the history of Jazz in the twentieth century. In particular, the “Clifford Brown & Max Roach” album released in 1955 is a must-listen record for every Jazz lover and aspiring musician.

Clifford Brown

This “September Song” version is from the 1955 “Sarah Vaughan with Clifford Brown” album, reissued in 1991. I chose this solo as one of my favorites because of how Brown made his horn sing in this performance. I mean, this is Jazz, but there’s also a lot of Blues and Soul in this improvised solo.

Brown almost sounds like a Blues guitarist during a few spots if you listen closely. Sure, he doesn’t sound like Clapton playing a Les Paul into a Bluesbreaker, but you don’t need that to play the Blues with your heart out.

Besides the more soulful sides of his playing, Clifford Brown was also a very creative bebop-era improviser. So you can expect to find humorously rhythmical fast lines always resolved elegantly, showing a massive amount of class. Once again, quite impressive, considering he was in his mid-twenties when recording this album.

Now, let me address the elephant in the room: Clifford Brown played trumpet, not guitar. Why am I talking about a trumpeter on a guitar-related website? To answer this question, you have to understand one thing about Jazz: the guitar is not “relevant” in it.

Don’t get me wrong, I’m not saying that guitar isn’t crucial in the history of Jazz, but the language and sound of the genre weren’t influenced by guitarists that much.

Trumpeters, Sax players, and Pianists are responsible for creating and developing the vocabulary of Jazz. Still, that doesn’t mean that guitar players shouldn’t play Jazz, quite the contrary! Jazz vocabulary sounds excellent when played on the guitar, but it is always a good idea to listen to other instrumentalists and learn their licks and phrases.

Playing lines “stolen” from other instruments rather than the guitar will also make you sound cool and unconventional, so why don’t you try that with this solo? It undoubtedly helped me out.

  • Sarah Vaughan – Vocals
  • Clifford Brown – Trumpet
  • Herbie Mann – Flute
  • Joe Benjamin – Bass
  • Jimmy Jones – Piano
  • Roy Haynes – Drums

“The record companies owe it to the future of Jazz to make every possible fragment of the beautiful musical gifts Clifford gave the world with unbounded love.” – Quincy Jones about Clifford Brown

John Pizzarelli – Route 66 (from 1:15 to 3:10)

John Pizzarelli is a Jazz guitar player and singer you could call a “child of art.” His father was the legendary swing guitarist Bucky Pizzarelli, who famously toured with Benny Goodman for many years.

Because John grew up with people like Les Paul, Clark Terry, and Benny Goodman around the house, nobody was shocked when he started to become the outstanding musician he is now.

John Pizzarelli

John Pizzarelli gifts us with an excellent and soulful guitar solo during this live performance of the classic Jazz-Blues song “Route 66”. First of all, you can feel John’s superb timing over a swing groove from the very beginning of the song.

Even when just accompanying himself singing, the origins of Jazz guitar are right in front of our eyes and ears when he’s playing small chords on the “two and four” beats only. When he launches into his solo, he wants us all to understand that he means business. And by “business”, I mean having a good time.

He is singing throughout his improvised solo, which suggests extreme maturity in a guitar player, especially when soloing over a Blues structure like “Route 66”.

When you’re playing what you’re singing (not the other way around), you are using your guitar just as a means to an end because we should never forget that the ultimate goal is to express yourself freely, with as few obstacles as possible.

So yeah, sometimes your scales, arpeggios, and all that stuff can be an obstacle when you want to express yourself on the guitar but don’t worry, you can always cut that out while you’re playing and let your ears dictate the sounds you’re going to produce.

The Pizzarelli name is synonymous with Swing, and John doesn’t deviate from that. He is utterly comfortable playing Jazz with an approach that some people could call “old-fashioned”. I agree with this, but you must understand that “old-fashioned” doesn’t necessarily mean “dated” when talking about music.

I believe that John Pizzarelli’s approach to improvisation is fantastic. There is no space for showing off, no desire to impress the other musicians in the crowd. John is there to groove and make the audience feel the swing beat and have fun.

Jazz became famous because it was easy to dance to, and people were doing that back in the 30s and 40s. Somehow Jazz ended up losing its groove and sadly became only a platform for musicians to show off, which pushed the larger crowds away. At some point, the Jazz musicians moved from the original purpose of their art form.

Luckily for us, musicians like John Pizzarelli are trying to keep the tradition of swing music going by playing their hearts out through improvised music that people (including the musician who is playing it) can sing and relate to.

  • John Pizzarelli – Guitar and Vocals
  • Martin Pizzarelli – Bass
  • Ray Kennedy – Piano

“…and everyone came through our house. I grew up with people like Benny Goodman, Zoot Sims in the house, playing right in front of me.” – John Pizzarelli

Terrace Martin – Can’t Help It (from 3:05 to 4:05)

When you listen to Terrace Martin for the first time, you will probably not associate his music with what a traditional Jazz musician might play, and you wouldn’t be wrong in doing that.

Martin’s music is not to be considered straight-ahead Jazz by any means. Still, it is the continuation of the glorious tradition of including external musical influences in music played with the Jazz mindset. Terrace Martin reportedly said: “I started producing hip-hop tracks because it was the music of my time, but I never lost my love for jazz”.

Like America’s most famous art form evolved into Fusion in the 70s, incorporating distorted electric guitars, synthesizers, and Rock drums, the “new wave” of Jazz music is heavily influenced by Hip Hop nowadays.

Martin is one of the musicians at the forefront of this new approach to Jazz music, along with top players like Robert Glasper, Kamasi Washington, Thundercat, and many more.

As a producer, Terrace Martin was heavily involved with one of the most exciting albums and also one of the overall best records of the last decade: “To Pimp a Butterfly” by Kendrick Lamar, released in 2015. This album represents the pinnacle of the fusion between Jazz and Hip Hop, in my opinion, and I advise you to check it out if you haven’t already.

Terrace Martin Favorite Jazz Solos

Although primarily a Saxophone player, Terrace Martin plays keys on this fantastic version of Michael Jackson’s “Can’t Help It”. Originally written by Stevie Wonder, this song is not your typical Jazz standard. Still, the underlying chord changes make this piece a perfect platform for modern Jazz musicians to improvise over, just like Martin wonderfully does over the chords for the verse and pre-chorus sections.

We can hear his more traditional Jazz influences during this performance. This solo flies through “spicy” extensions and funky note choices, especially towards the end when Terrace Martin tributes John Coltrane with an arpeggio-ish phrase that sounds like it’s from one of the saxophonist’s iconic recordings from the 60s.

The instrument that Martin uses to solo is called a vocoder. The microphone he is using is not amplifying his voice like a regular mic. It picks up the different vowels and consonant sounds, feeding them into the keyboard. So he is basically “sculpting” the sound of his keys.

This way, you can pronounce words and use the keyboard to pitch them in real-time, creating polyphonic sounds otherwise impossible to reproduce. If this is not self-expression, then I don’t know what is.

  • Terrace Martin – Vocoder and Bass
  • Neka Brown – Vocals
  • Marlon Williams – Guitar
  • Kenneth Crouch – Keys
  • Trevor Lawrence – Drums
  • Quincy Jones – Producer

“You gotta keep it broad. Cause Jazz is not the only thing in life moving. Neither is Funk. Neither is Rap. Neither is Rock. It’s everything.” – Terrace Martin


Question: Do I Have to Learn Solos in Their Entirety?

Answer: It depends on what you want to take from the specific solo you wish to learn. If you like only a few licks in a performance, there’s nothing wrong with learning only small sections of other people’s solos. As long as you understand the context that you’re going to extract these chunks from, you should be fine.

On the other hand, if you like a solo in its entirety, and maybe you want to learn how the solo is structured, you should probably study the entire thing. Bear in mind that, whichever approach you choose to have, you don’t have to learn everything note by note religiously. You can adapt licks and phrases to your playing right away!

Question: How Should I Approach Learning Other People’s Solos?

Answer: I suggest you do that by ear as much as possible, but you could also use transcriptions made by other musicians to double-check what your ears are telling you.

Training your ears to associate the sound of a specific note with the physical movements you need to make with your hands to play that same note on the guitar is key to successfully improving your improvisational skills.

Question: Is it That Useful to Learn Somebody Else’s Solos?

Answer: It is. Believe me. There’s no way around it if you seriously want to get better at playing guitar. As I said before, this all makes sense if you accept the concept of music being a language. People learn languages effectively when they adopt a practical approach.

So, if you want to get into Jazz or any other form of improvisational music (like Blues), I advise you to start by trying to copy master players as much as possible. Even if it doesn’t feel remotely close to the original, you should keep your head down and go through this process. We are all native speakers of our mother tongue, aren’t we?

Question: Should I Learn the Solos Cited in this Article?

Answer: If you want to, why not? It will certainly not harm you if you choose to learn these solos. Still, you should only transcribe and play solos you like. Studying somebody else’s solo is a long process, and it can take days or weeks to learn how to play even a one-minute solo. So, if you like any of my five favorite Jazz solos, please go ahead and practice away!

Top Jazz Solos – Conclusion

So, I just showed you five of my favorite Jazz solos. By the way, they’re not in any specific order. I don’t have favorites. And how could I? These are all fantastic performances by outstanding Jazz musicians.

We went from the traditional sounds of Wes Montgomery and Clifford Brown to the modern approach of Terrace Martin, passing through the swing faithfulness of John Pizzarelli and the personal approach to Bebop of John Scofield. What a trip!

Jazz improvisation is one of the fascinating aspects of music to me, and I hope I have given you a varied perspective on what it means to play with a Jazz mindset. It doesn’t matter if you play with or without overdrive. It is not essential whether you choose to play a hollow-body Jazz guitar or a Strat.

What matters is the music you make when you are improvising at the moment, with or without other musicians. Improvisational music is about unfiltered honesty, and if you manage to get to a level where you can experience such freedom regularly, you are living the dream!