Peewee Longway emerged as one of the last new members of the old 1017 before Gucci Mane’s last period of incarceration, popping up in 2013 and 2014 on early Young Thug tracks. Since the boss Mane’s release from prison in 2016—followed by Gucci’s crossover success, healthier rebrand, and Master P-type pivot to mentor of “The New 1017”—Peewee has mostly struck out on his own, orbiting Atlanta’s rap scene as a perpetual, determined independent, the head of his own MPA Bandcamp label.
He’s cited by peers as something of a mover and shaker behind the scenes, even as mainstream momentum has slightly eluded him—he helped facilitate Migos’ original deal with Quality Control, and Gucci Mane credits Peewee with introducing him to the enigma and icon that is Thugger, one of the most fruitful and paradigm-shifting creative relationships of rap’s last decade. Most recently, Peewee has positioned himself as part of a tag team with fellow Georgia self-starter and crypto-entrepreneur Money Man; together the two are a classic opposites-attract odd couple pairing, Money Man like a more menacing Red Power Ranger to Peewee’s goofier “Blue M&M.”
The first Longway Sinatra might have had the swagger, but it lacked close-to-the-mic crooning. On Longway Sinatra 2, Peewee pulls the listener closer for some of his most intimate and introspective tracks yet—call it In the Peewee Small Hours. He’s now something of a link between multiple eras of regional hip-hop history—the rap game Rat Pack of Longway Sinatra 2 is made up of everyone from legendary Memphis producer Jazze Pha, to new stars in the Southern constellation like Lil Baby and Blac Youngsta, to similarly underrated Atlanta workhouse Hoodrich Pablo Juan.
Peewee has long leaned into the cartoonishness suggested by his name, rapping with a playful candor. It’s an image enhanced by his delightfully absurdist mixtape covers, usually designed by surrealist mixtape visionary KD Designz, casting Peewee as pieces of candy or bowls of spaghetti. Even his play on Ol’ Blue Eyes feels more like a Dick Tracy comic book character than a signification of slickness or timeless cool, as Sinatra is for perpetual cornball Logic. There’s a kind of cheeky self-deprecation to Peewee’s lyricism; not many rappers would dare compare the itchiness of their trigger finger to their struggles with chronic premature ejaculation and then make a hook out of it, as he does on “Anxious.”
Cassius Jay displays a malleable hand when it comes to production, backing up Peewee’s various vibes like Sinatra conducting a spectrum of colors. Grinding tracks like “White Horse” and “Takeoff” recall Jay’s work on Future’s DS2 with growling drums, laser blast synths, and icy bells. But he’s equally adept at soundtracking the softer and sweeter side of Peewee’s playboy persona, draping “Pink Salmon” in bright keys and bringing “Blue Benjamins” to a decadent MBDTF-like climax with a shredding guitar solo.
In the past, Peewee has rapped from the perspective of a non-stop hustler at the frontline of various illicit industries, but on Longway Sinatra 2 he occasionally zooms out to the bird’s eye perspective and reflects on the emotions and memories behind him. “Heaven Got a Ghetto” is the kind of track you can only make once you’re nearing middle age, a thoughtful and almost gentle reflection on the vast changes decades can bring.
Over a clean electric guitar line on “Skydiving,” Peewee reminds us that Atlanta, despite having become a new money media metropolis, is still deep in the heart of the country. He effortlessly slides into a Southern sing-song drawl for an authentic country-rap fusion, with few novelty signifiers beyond some bars about riding horses. It’s not exactly a melodic interpolation, but the chorus—“Skydiving/Now she on Rocky Mountain climbing”—gestures toward Tim McGraw’s bleeding heart power ballad “Live Like You Were Dying” (from the album of the same name, a raw and self-hating pop reflection on the loss of a parent that’s like the 808s & Heartbreak of radio country).
“Blue Benjamins” flips “I Would Die 4 U” for a tribute to the love of the game—“I will die for these blues”—that would have been right at home during Southern rap’s golden age of mixtapes, next to the shelf alongside Yo Gotti and Gucci Mane’s “Pure Cocaine.” It’s fitting that a Prince riff is a prime showcase for the flexibility of Peewee’s voice, slipping between his usual delivery, a deeper rumbling mumble, and stretches of Thug-like falsetto. Peewee has long been one of Atlanta’s most dependable and essential emcees, even if he never acquired the national stature of some of his comrades, but Longway Sinatra 2 suggests an artist who, just like the chairman of the board, will only develop and complicate with age.
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