MASSPIKE MILES

Masspike Miles is the stage name of Miles Wheeler, a Boston rapper. He entered the music industry as a teenager as the lead singer of Perfect Gentlemen, a group put together in Boston in 1988 by producer Maurice Starr — their second album was released on Warner Bros. Records in 1993, with "Miles 'Masspike Miles' Wheeler" credited as a member.

His own YouTube channel describes him simply: "As a Boston native, my journey has been all about turning life's stories into soulful melodies."

In 2008, Masspike Miles was signed to Rick Ross's newly-founded Maybach Music Group, among the label's first acts alongside Triple C's — sources differ on which of the two was technically first, and this profile does not assert either claim as settled. His MMG-era work includes The Road Less Traveled (2011) and the original Say Hello to Forever mixtape (January 2012), both explicitly hosted by Maybach Music Group.

By 2013, press coverage described him as a former MMG artist. From 2011–2012 onward, his catalog has been released independently through his own Inkkwell imprint.

His most recent album, 11 Highland Ave, was released July 11, 2025, followed by the singles "Hellos to Goodbyes" (feat. Erick Sermon, January 2026) — billed as the first single from an upcoming album, 77 Richfield St. — and "Dive" (January 2026).

His catalog documents a long-running, still-active relationship with Termanology, spanning "You Should Go Home" (2010), "Where's the Love" (2016), and continuing into 2026 releases. He has also recorded directly with Statik Selektah, Ea$y Money, and Smoke Bulga, and appears alongside Millyz, Slaine, and Edo G on the 2014 Boston posse cut "Boston vs. Everybody."