Three shows and two musical parties to attend this week

Once again, our man Sgt. Tiki has surveyed the musical landscape and selected the best of what’s happening locally for your musical enjoyment and edification.

Whether your tastes run to film synth-y indie, classic reggae, or raunchy rap, you’ll find something to satisfy your audio appetite.

Headphone

Synth-forward indie electronic band Headphone was founded in 2014 by Morgan McRae (who studied piano and business management at St. Louis University) and drummer Philip Cullin. The duo was later joined by bassist Darren Goldberg (who co-owns Foxhole Studios with McRae) and guitarist Nick Costa. “Our music blends our interests in everything from classical and jazz to electronic and independent rock,” according to the band, “while the lyrics look at the enigmatic space between connection and detachment, hopefulness and despair.” Known for a dynamic alt-electro sound, blending energetic, gritty rock with electronic elements, their music is characterized by an indie/alternative style, with recent work focusing on high-energy, guitar-driven indie music Their album Sector 1 was released in 2015, followed in October 2016 by Clouds of Scattered Noise, with their newest release being Sledgehammer. You can get a taste of their Winstons gigs on Youtube, where they’ve uploaded a video of them performing “Ready Steady Run” at the OB venue.

• Where: The Holding Company, 5046 Newport, San Diego
• When: Friday, February 20, 2026 at 7:30 pm
• Ages: 21+
• More info

Tribute to reggae legends

The 45th annual Tribute to the Reggae Legends, also known as Bob Marley Day, honors the rich cultural and musical legacy of reggae. Founded by Prophet World Beat Productions, the event promises a powerful message of unity, peace, and awareness of social inequities. Thanks to pioneering artists such as Bob Marley and Peter Tosh, reggae music continues to unify as well as entertain. This celebratory concert will span two days with both local and national acts slated to perform. The Friday bill includes Julian Marley & the Uprising, Johnny Osborne & Fully Fullwood Band, Mara Sulu, Pinnacle, and DJ Mykol Orthodox. Saturday features King Yellowman, Ginger Roots, Johnny Clarke, Marlon Asher, Ranking Joe, Quinto Sol, Chezidek, and more.

• Where: World Beat Cultural Center, 2100 Park Boulevard, San Diego
• When: Friday, February 20, 2026, at 7 pm and Saturday, February 21, 2026, at 3 pm
• Ages: All ages
• Get tickets

Steve Poltz’s 17th Annual 50th Birthday Bash

Steve Poltz’s new album JoyRide is his 14th solo album and first new LP in close to four years. The record was produced, engineered, and mixed by Dex Green (known for his Grammy Award-nominated work with such artists as Shemekia Copeland, Elvis Costello, Margo Price, and Nicole Atkins). It was preceded by a single for “If It Bleeds It Leads.” Says Poltz, “I used Emmylou Harris’s rhythm section: Bryan Owings on drums, and Christopher Donohue on bass. Dex Green played this weird-sounding keyboard that added to the whole vibe, along with my acoustic guitar. I wrote the song after watching the news with some people who were yelling at the TV screen. I had to leave the room and immediately write this song.” Another single dropped recently for “Love a Little Bigger,” co-written with longtime pal Vince Herman of Leftover Salmon, and the album track “Fixin’ Up” is a three-way co-write with Americana icon Jim Lauderdale and 2018 CCMA Songwriter of the Year, Skip Black. The Saturday February 21 show will feature a reunion performance by his one-time band The Rugburns, alongside Gregory Page.

• Where: Belly Up Tavern, 143 S Cedros, Solana Beach
• When: Saturday, February 21, 2026, at 8 pm and Sunday, February 22, 2026, at 8 pm
• Ages: 21+
• Get tickets

CupcakKe

Rapper, singer, and songwriter CupcakKe rose to fame via SoundCloud and TikTok, where her explicit lyrics are frequently used in memes. Known for her bold, hyper-sexualized and often humorous lyrics, she blends raw and explicit sexual content with themes of LGBTQ+ advocacy and female empowerment. Despite the explicit nature of popular tracks including “Deepthroat” and “Vagina,” albums like Ephorize and Eden, have received critical praise for their artistic aspirations and production. Her debut mixtape Cum Cake appeared on Rolling Stone’s list of the Best Rap Albums of 2016 at number 23. Beyond sexual content, she also addresses topics such as childhood trauma and mental health, evincing an ability to be both raunchy and deeply personal, showcasing confidence and tackling taboo subjects with both humor and depth. She’s touring in support of her sixth full-length, The Bakkery, released last October.

• Where: House of Blues, 1055 5th Avenue, San Diego
• When: Sunday, February 22, 2026 at 7:30 pm
• Ages: 18+
• Get tickets

San Diego Music Awards nominee announcement show

Established in 1991, the 35th annual San Diego Music Awards are at hand. Covering diverse genres—including Rock, Jazz, Hip Hop, and Americana—the event highlights local talent and serves as the primary fundraiser for the San Diego Music Foundation’s Guitars for Schools program, which has placed guitars in over 123 schools, raising over $800,000.00 to foster music education. Although the actual award show doesn’t take place until May 6 at Humphreys by the Bay, the nominees will be announced at this Little Italy event which will feature live performances previewing what to expect on Shelter Island. Doors open at 6pm for a bill that includes Matthew Phillips, who won Best Pop Artist at the 2024 and 2025 San Diego Music Awards. His debut album Till It’s Over has earned 138,000 Spotify streams, with around 15,700 Monthly listeners, and his Spotify account has over 817,000 views, with Till It’s for 574,000 of them. Also appearing is singer-songwriter Cheyenne Benton, who was born in California City near Lancaster before relocating with her family when they moved to San Diego just before she turned five. Among the influences she cites are Taylor Swift, Maroon 5, the 1975, Lorde, Pale Waves, Kim Petras, Carly Rae Jepsen, Ke$ha, and Transviolet. Her song “Drinkin’ About U” earned a nomination for Best R&B, Funk, or Soul Song at the 2023 San Diego Music Awards, and her sophomore album Corrupted dropped last August. The bill includes The Bastards and Patch & Maggie.

• Where: The Music Box, 1337 India Street, San Diego
• When: Monday, February 23, 2026 at 7:30 pm
• Ages: 21+
• Get tickets