Top 5 Guitarists of All Time (Or, Just Those I Am Listening to Now)

2026-05-31T21:39:00Z

The other day, a good friend of mine asked me over the group chat who my "Top 5 Favorite Guitarists of All Time" are. Since answering that question is impossible, I am instead going to name the first five guitarists I could think of based on songs I have been listening to recently. So, keeping that recency bias in mind, here they are (in no particular order), some of my favorite guitarists:

George Benson

Most listeners will recognize George Benson from his 1976 smash hit "Breezin'", which helped usher in the smooth jazz era and for a time was a fixture of supermarket background music heard across America (alongside Chuck Mangione's "Feels So Good"). But don't get it twisted—George Benson is a certified guitar hero. I am most familiar with his output on CTI records, because records released on that label were very easy to find on the second-hand market back when I was collecting a lot of vinyl. Here is one such song from his 1976 album, Bad Benson, called "The Changing World" (hip-hop fans may also recognize this one):

Scott Henderson

I first heard Scott Henderson by way of The Chick Corea Elecktric Band, specifically their eponymous debut album. And while credit goes to Carlos Rios for the guitar work on my favorite song on that album, "Cool Weasel Boogie", Henderson contributed some fantastic guitar work on that album as well. That said, the latter is probably more well known for his output with his band, Tribal Tech. Their 1987 track "Mr. Hee" is a standout, with it's mysterious Eastern (albeit somewhat Orientalist—check the album cover) feel, glassy FM keyboards, and phenomenal lead and rhythm guitar work by Henderson.

Chuck Schuldiner / Andy LaRocque

OK, I am kinda cheating on this one because I've listed two guitarists here. But bear with me, because both are integral to the amazing guitar work heard on Death's "Trapped In A Corner", from the 1993 album Individual Thought Patterns. Death was essentially Schuldiner's project, with various players drifting in and out of the rotation over the years. King Diamond's Andy LaRocque makes a guest appearance here, offering a jaw-dropping solo at the track's midpoint, accompanied by Chuck's potent, syncopated riffing. Chuck adds his own blistering solo to close out the proceedings. This really represented the apex of technical death metal and guitar pyrotechnics at the time, and it remains to this day a classic of the genre.

Wes Montgomery

Arguably the best jazz guitarist of all time, Wes Montgomery's influence on both jazz and generations of guitarists is undeniable. In particular, I love his solo on the Gary McFarland penned "13 (Death March)", which appears on the 1968 collaborative album Jimmy & Wes: The Dynamic Duo album, co-starring Hammond B3 virtuoso Jimmy Smith. Wes' guitar solo is a masterful demonstration of musical restraint and melodic phrasing, and his octave vamps are instantly recognizable.

Tony MacAlpine

I listened to a lot of shredders when I was in high school, back when I was (somewhat) seriously pursuing guitar. Naturally, I listened to Yngwie Malmsteen, Steve Vai, Joe Satriani, and Tony MacAlpine. And of course, Eddie Van Halen and Randy Rhoads were both huge influences on my musical education. That said, outside of Eddie & Randy, I don't really listen to those guys that much anymore, but I do find myself going back to Tony MacAlpine regularly. While he can obviously shred like nobody's business, more importantly, he writes good songs with interesting melodies. As far as albums go, I think Maximum Security is probably his most cohesive and consistent effort from his eighties hair metal phase. But if I had to name one song, it would be "Stream Dream", off of 1992's Freedom To Fly. It is such a euphoric, energetic, and wonderful song. Also, it totally reminds me of console games I played growing up in the 90s, imbuing it with a nostalgic quality that brings me a lot of comfort.

dtg

Top 5 Guitarists of All Time (Or, Just Those I Am Listening to Now)

George Benson

Scott Henderson

Chuck Schuldiner / Andy LaRocque

Wes Montgomery

Tony MacAlpine