Sir the Baptist
William James Stokes, a preacher’s kid—one of twenty-two!—has brought his unique brand of “healing hip-hop” to appearances at Lollapalooza, Bonnaroo and Made in America and opened for Beyonce, Lauryn Hill, Alicia Keys, Mary J Blige and Nelly, and is probably the only person with that résumé who has also appeared with Joel Osteen Ministries. In 2019 he launched Tymple, which he described to JamTV as a “way to explore your faith without the dogma of religion. It allows you to go into your own journey of spirituality without worrying if ‘I’m doing it right’ and it gives the education and tolerance of religions that may not be your own.” Tymple is a Spotify API that channels spiritual content, starting with Christianity, Islam, Buddhism and Judaism and which they plan to broaden to other faiths. Just as Sir is expanding the audience for gospel with hip-hop, he hopes that Tymple will expand gospel beyond Christianity. He released the album “Godfidence: Kingdom Bae” via Tymple in early 2020.
South Side rapper Dreezy (born Seandrea Sledge) dropped “Big Dreez” in 2019, with a luxury supporting cast including Kash Doll, Jeremih (their second duet), Jacquees (whom she used to date), Offset and Derez De’Shon. She was part of a luxury cast herself, with her contribution to Dreamville’s “Revenge of the Dreamers III” (“Got Me” teamed Dreezy with Ari Lennox, Ty Dolla $ign and Omen). Dreezy promises a full album, but at her own pace. She’s dipped a toe into acting—she has a role in Chris Robinson’s 2019 Netflix coming-of-age drama, “Beats”—and keeps a high profile through modeling gigs. She’s a brand ambassador for Rihanna’s Savage X Fenty, among other assignments. Her fashion-saturated Instagram page boasts 1.2 million followers.
Jayson Mick Jenkins may have Huntsville, Alabama roots, but he attended Young Chicago Authors open mics at seventeen, and today at the relatively mature age of twenty-nine, he’s a Chicago fixture. In the past two years he’s dropped his second full-length, “Pieces of Man,” and two EPs, 2018’s “Or More; The Frustration” and this year’s “The Circus.” The latter features a track, ”Carefree,” in which he raps that “If you’re living carefree you probably don’t look like us,” a phrase of such importance that he sells it on a hemp T-shirt. Along with Prop, J-Stock, Burman and Maine The Saint, Jenkins is a member of Free Nation, which calls itself “a hip-hop group that promotes creative thought without accepting narrow views imposed by the powers that be.”
Cadien Lake James, Clay Frankel, Jack Dolan, Colin Croom and Connor Brodner—“the dudes,” as hometown fans refer to them—have been around long enough to be considered elder statesmen rather than enfants terrible. And while their live shows (which, until the pandemic, were frequent and far-ranging) remain supercharged, there’s evidence on their latest album—2019’s “Lookout Low”—that they’re experiencing mid-career drift, as they try to figure out who they’re meant to be now that they’re no longer brash young upstarts. The album has sold well enough to give “the dudes” the time and freedom they need to retool their brand, and a series of singles (the most recent being January’s “Cawfee” and “St. Vulgar St.”) show that they’re on it. Meanwhile, they’ve just dropped (in June) an EP, “Side A,” featuring four new songs that were in the works when the shutdown began, and that the intrepid bandmates rolled up their sleeves and completed remotely.
2019 was Woods’ breakout year, as the singer-songwriter released her high-profile “Legacy! Legacy!” album, each track of which was inspired by a cultural icon—ranging from Zora Neale Hurston and Eartha Kitt, to James Baldwin and Jean-Michel Basquiat. Our reviewer noted that the tunes “are named after the major figures in the singer’s artistic pantheon, but the tunes aren’t about them. They’re about the impact those artists have had on the woman singing them. The passion and integrity that comes through each tune makes it clear—Woods herself is the legacy.” The album features a luxury cast of guest artists, including Saba and Nico Segal, racked up critical hosannahs, and several tracks inspired lavishly produced videos. Woods toured the album both domestically and abroad, and would still be on the road if the pandemic hadn’t gotten in her way. At this point, it seems like a pandemic is the only thing that could.
Robert Rodi is an author, spoken-word performer and musician who has served as Newcity’s Music Editor since 2014. He’s written more than a dozen books, including the travel memoir “Seven Seasons In Siena,” and his literary and music criticism has appeared in the Los Angeles Times, the Chicago Tribune, Salon, The Huffington Post and many other national and regional publications.