Hip-hop’s 50th anniversary in 2023 sparked a renewed interest in the history of the genre, from DJ Kool Herc’s legendary (possibly apocryphal) invention of scratching at a party in the Bronx, to being the most popular genre in the world today. These histories have tended to focus on cities like New York, Los Angeles, Oakland, and Atlanta. Perhaps going a little deeper, some people might talk about Houston, Chicago, Detroit, Philadelphia, and New Orleans. Nowhere, however, is Boston’s rich hip-hop history discussed in all that much detail (it’s not just Marky Mark), and I think that’s a shame. So allow me to rectify the situation. These are five songs (in no particular order) that showcase the best of Boston hip-hop:

1. Akrobatik, “Say Yes Say Word” (1999)

“Say Yes Say Word” was one of the very first singles put out by this Dorchester native, and it remains his best. Over a minimal, bass-heavy beat, Akrobatik spits some of the most stylishly boastful bars ever put on wax. My personal favorite is “No time for slacking during the verbal slaughter/The sharks the other way when I’m in the water.” 

2. L Da Headtoucha, “It’s All Over” (1997)

It is my unwavering opinion that L Da Headtoucha is one of the most criminally underrated rappers ever. In the late 1990s, the Worcester emcee was featured in The Source magazine and made several appearances on Stretch and Bobbito, before disappearing into obscurity. This underground gem comes off The 1997-1998 Demos EP put out by Chopped Herring Records in 2019 and features L’s signature lyricism over production from the Vinyl Reanimators (also from Worcester).

3. 7L & Esoteric, “Protocol” (1997)

First released as part of the Rebel Alliance compilation on Boston’s own Brick Records, “Protocol” is one the songs that put 7L and Esoteric on the map. Esoteric’s lyricism is in full effect on this track, perfectly complemented by 7L’s laidback beat. Also check out Czarface, 7L and Esoteric’s collaboration with Wu-Tang’s Inspectah Deck.

4. Scientifik, “Lawtown” (1994)

Coming straight out of Lawrence (or Lawtown), Scientifik is another rapper who was gone too soon. He released only two albums during his lifetime, the second of which spawned this masterpiece of storytelling. Over a dark, jazzy beat produced by fellow Boston legend Edo. G, Scientifik rhymes about the dangers of street life in Lawrence. 

5. Da Headtoucha, “Stretch Armstrong Freestyle” (1997)

Truthfully, there’s not a lot of information available about this track, other than the fact that it was released as part of Stretch Armstrong’s Lesson 1 tape. I don’t know when it was recorded or who produced it (probably either Stretch or the Vinyl Reanimators). What I do know, however, is that this song is an incredible display of lyricism and flow: “My aura shines purer/aggressively my method be something you ain’t sure of/lyrical explorer.”

6. (Bonus) Raw Produce, “Cycles” (1995)

I couldn’t end this list without mentioning something from Cambridge. Just check it out.

This article also appears in our January 2024 print edition.