8 Fun Challenging Guitar Songs

Any list is subjective, but when it comes to a list of songs or artists, the opinions can vary even greater. After teaching guitar for 20 years, I’ve learned to appreciate almost every style. So, I included tunes that have affected my playing the most and have been super fun to play. Each of these tunes, for different reasons, had me sitting and playing my guitar for hours. So, let’s dive into 8 fun challenging guitar songs.

“Pride and Joy” by Stevie Ray Vaughan

We start our journey off in the styles of the late great guitarist Stevie Ray Vaughan. This song is deceptively hard. If you are looking to improve your right-hand rhythm technique, this song is a must. This is the basis of Texas Swing. The hardest part about this song is mastering the art of muting adjacent strings while isolating a note or grouping of notes. Not to mention, this song is chock full of staple blues riffs. Make sure to check out several versions of this song, as Stevie plays it the same twice.

“Sweet Child O’ Mine” by Guns N’ Roses

Second on our list is a hairband classic. I underappreciated Slash as a guitarist until I started teaching guitar. One of my students asked me to learn this tune, so we learned it together, and immediately I understood why Slash was such a popular guitarist. This song is a great study for phrasing and having a common theme to build your solo around. The run in the middle of the solo climbing up to the climactic second half of the main solo is a classic and difficult run. “Sweet Child O’ Mine” is a good study of using the harmonic scale well.

“Satch Boogie” by Joe Satriani

Satriani is one of the original guitar heroes. From a rocking main riff to tapping mayhem, this song is loaded with fun guitar riffs. The solo section in this song is a lesson on how to be tasty. You will need a good understanding of how to use a whammy bar to get the true sounds happening. The tapping section at the end is basically an exercise and is super fun to play once you get it. (honorable mention “Hot for Teacher” by Van Halen)

“Gitarre 2000” by Doyle Dykes

This is one of the more obscure tunes on the list, and quite frankly, I would not have discovered this song without the request of my student. Perhaps my favorite riff in this tune is the harmonic riff in the beginning. It’s amazingly fun to play and it has been an impressive party trick for my musician friends to this day. The rest of the song is quite difficult, beautiful, and well worth the effort that is required to master this tune.

“Dolemite” by Scott Henderson

If you are looking for a foundation for jazz fusion. Look no further than Scott Henderson. You’ll find a smoking riff, blistering runs, and amazing outside melody lines. This song taught me how to create tension and release, how to play outside lines well, and how to construct a solo in a way to build the dynamic and keep it interesting. This is not a song for the faint of heart.

“Hot Wired” by Brent Mason

Now, we step over into the hot country world. Brent Mason is a legend. He has literally played on EVERY famous country artist’s albums. If you don’t believe me check out his tracklist. On his solo effort, he cuts loose and lets some blazing licks fly. This song will kick you in the rear with chicken picking, flat-picking, bends, and a lick library of hot country guitar licks. For an extra challenge, try to play it like Brent with a thumb pick and alternating between your thumb and middle finger on your right hand.

“Cliffs of Dover” by Eric Johnson

This very well may be one of the most famous instrumental guitar songs of all time. Heck, my wife even likes to listen to this one. That’s because Eric’s chorus melody is extremely catchy, and it’s super fun to play. It’s quite addictive. However, around said melody are several brutal licks that will require a LOT of time to execute well. This song is a test of technical prowess. One of my favorite techniques I learned from EJ is to mix up the patterns I play and to incorporate scalar patterns of 6, 5, 4, etc. If you decide to embark on this journey, set aside a good bit of time.

“Capricho Árabe” by Francisco Tárrega

I wanted to throw you a curveball for the end of our list. Tárrega is the OG guitar hero and grandfather of classical guitar. He was a rock star in his day, playing in small parlors and entertaining crowds. Almost all of his tunes are fun to play, but this one is a massive undertaking. I did not start as a classical or fingerstyle player. So, I had to backtrack, learn proper finger technique, and dedicated countless hours on this tune. The left-hand technique and stretches can be as challenging as the right-hand techniques required for this song.

There you have it. This is my list of some of my favorite and most influential tunes I have learned and/or taught over the years. I hope you enjoy them and best of luck to you, should you decide to give any of these a shot.