If the title “I Never Loved Myself Like I Loved You” didn’t stir up any feelings, singer/guitarist Jack Underkolfer of Dead Poet Society makes sure the itracks introspective name and revealing lyrics don’t go unnoticed with his emotional performance of the song on the latest edition of Press Play At Home.  

With lyrics like “the self-loathing comes and goes” and “maybe you could show me another way out”, the track fits the hardened self-reflection that Dead Poet Society displays on their 2021 full-length debut album -!-.

Despite the painful lyrics about self-hate, Underkofler’s masterful execution of the song makes “I Never Loved Myself Like I Loved You” a track to revisit.

Watch Underkofler’s gripping performance above and click here to enjoy more episodes of Press Play At Home.

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On "Dear Life," R&B singer Genia pens a farewell letter to her lover — while simultaneously reflecting on how the intense saga crumbled her.

"I can't take anymore/ Put my pride aside, thought you could save me," she cries in the first verse. "These days, I don't know what I need/ You destroy me from the inside out/ If I go off the deep end/ You'll be sure not to bring me back."

In this episode of Press Play, watch Genia deliver a stripped-down performance of the vulnerable track alongside her guitarist.

The California native released "Dear Life" on Nov. 10, via Def Jam Recordings. She has also dropped three more singles — "Like That," "Know!," and "Let Me Wander" — leading up to her sophomore mixtape, 4 AM In The Ville, on April 19. 4 AM is a sequel to her debut, 4 PM In The Ville; both projects are inspired by Genia's experience of growing up in Victorville, California.

""[The songs] explore the different stages of grief in a relationship," she revealed in an interview with Urban Magazine. "The second tape is really me touching on falling in love, betrayal, anger, and rape."

Watch the video above to hear Genia's acoustic performance of "Dear Life," and check back to GRAMMY.com for more new episodes of Press Play.

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Now in her early twenties, R&B rookie Kenya Vaun would give anything to return to her childhood adolescence — the days of block-turned-house parties and no bills.

"Feels like it was only yesterday/ And life was so easy yesterday," Vaun raps in the chorus of her new song, "Yesterday." "If I had the chance to do it again/ I'd do it the same/ The joy and the pain/ The coldest of winters/ The summertime rain/ No, I wouldn't change my yesterdays."

In this episode of Press Play, watch Vaun deliver a live rendition of the track, straight from the recording studio.

"Yesterday" arrives on Vaun's latest EP, The Honeymoon Phase, which dropped March 22 via 300 Entertainment. She also released an accompanying music video, filmed in her hometown, Philadelphia.

"'Yesterday' talks about my experiences when I was younger because that is a huge part of what made me who I am today," Vaun said in an interview with Rated R&B. "Seeing how times are today, it's kind of like, 'Dang. Imagine if I grew up during this time.' I don't know how I would be, like, for real."

Watch the video above to hear Kenya Vaun's nostalgic performance of "Yesterday," and check back to GRAMMY.com for more episodes of Press Play.

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On "Constellations," pop singer and social media star Jade LeMac has stars in her eyes after a passionate moment in love.

"Your freckles lead the way/ I trace your constellations," LeMac sings in the chorus. But as the two leave each other's arms, it's like they're a galaxy away: "Now, you're gone in the blink of an eye/ I try to remember what you look like/ Orion's Belt in the sky/ Closest thing to you other than my mind."

In this episode of Press Play, LeMac delivers an at-home performance of "Constellations," stripping down the wavy track with just an acoustic guitar.

Initially released in 2021 via Arista Records, "Constellations" was LeMac's debut single, and eventually became the title of her 2023 debut EP. Nine months after releasing Constellations, LeMac delivered another EP, titled Confessions — and on March 1, she gave it the deluxe treatment.

"['Constellations'] started this whole journey, and I wouldn't be here without it," she said in a statement about the song, which went viral on TikTok after being featured in Netflix's My Life with the Walter Boys. "I have learned so much about myself, my songwriting, and storytelling."

Watch the video above to watch Jade LeMac's lovesick performance of "Constellations," and check back to GRAMMY.com for more new episodes of Press Play.

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On "In 2 Deep," R&B newcomer Chikoruss makes one thing clear: he's blasé about any potential lover's relationship status. If he feels a spark, he'll follow that connection and consider the consequences later.

"I know you got a man, but I don't care," he boldly declares in the first verse. "Honestly, you should really make more time for me/ F— around, find out, you gon' see/ No matter, they say this love the same."

In this episode of Press Play, Chikoruss performs an acoustic rendition of the assertive single.

"In 2 Deep" is the Montreal native's premiere track with 300 Entertainment. As Chikoruss explained in a press release, the song is special to him because he made it during his first trip to LA. "It was the day I dropped my debut single, 'Body Language,'" he recalled. "I was beaming off of the good energy from the release."

Chikoruss' rookie year also saw the singer opening up for Bryson Tiller at the Toronto show of his 2023 tour. As he continues to craft "the Chikoruss sound," his goal is to create more tracks like "In 2 Deep," which channel the 2000s with a feel-good, modern approach.

Watch the video above to hear more about Chikoruss' fearless pursuits in love in this live performance of "In 2 Deep," and check back to GRAMMY.com for more new episodes of Press Play.

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