Singer-Songwriter Jill Sobule “Filled The Room With This Whirlwind of Whimsy”

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This week, the music world was taken aback by the news of Jill Sobule’s passing in a house fire outside Minneapolis at the age of 66 on Thursday. Sobule, admired within the songwriting community for her political activism, made her mark in the ’90s with songs like “I Kissed a Girl” and “Supermodel.” The former was historically significant as the first openly gay song to reach the top 20 on the Billboard charts, while the latter gained fame through its inclusion in the 1995 film Clueless.

One of the numerous friends of Sobule who are struggling to come to terms with the news is Michelle Lewis, a long-standing friend and the CEO of Songwriters of North America. For years, Lewis and Sobule have collaborated frequently since they first met in the mid-2000s. They had plans for Lewis to host Sobule in her Los Angeles home next week when she visited town, but sadly, that meeting will no longer take place due to Sobule’s passing.

Lewis shares that she’s “still struggling to get over the shock” as she continues to process the events. She describes her subject as “almost ethereal, simply captivating.

In an interview with The Hollywood Reporter following Sobule’s passing, Lewis characterized her friend as a unique author, fueled solely by her individual creativity, and a free-spirited artist who lived her life on her own terms.

Jill stood out unlike any individual you’ve ever encountered before. It’s a familiar statement, but when I say she’s unique, it’s not just figuratively speaking – she was the sole person like her. Analogies that involve humans don’t quite capture her essence. She embodied magic, radiance, exceptionalism, and uniqueness. I can’t imagine her as a typical human; she transcended the norm. People often refer to Chappell Roan as an artist’s favorite artist, but Jill was more than that – she was the songwriter’s muse, the singer-songwriter‘s idol.

Jill was exceptionally unique and incomparable to anyone you’ve ever met before. I use this term not just figuratively but literally – there was no other person like her. It’s challenging to find human comparisons for her as she transcended the norms of humanity. She embodied an extraordinary, radiant, and original spirit that was hard to put into words. I couldn’t think of her as a typical human; she was something beyond ordinary. People often call Chappell Roan an artist’s favorite artist, but Jill was more than just a muse – she was the songwriter’s inspiration, the singer-songwriter’s role model.

In my perspective, it wasn’t just her music and songs that mirrored her life, but her very existence. I’d say she was more like a nomad, rarely settling down. Her location was always uncertain – whether she was in New York, Los Angeles, or on tour – and that’s one of the captivating aspects about her. She had this enchanting knack for filling any space with a whirlwind of charm and spontaneity.

Kay Hanley (from Letters to Cleo) and I once formed a band known as The Dilettantes. Members came and went, with Lisa Loeb and Tracy Bonham among them, collaborating on songs with us. Nina Gorden was also part of the group. Jill first joined us to contribute to a Dilettante song, finding it enjoyable to write with two other women. She drew us into her world just as we had drawn her into ours. I received the devastating news from Kay, who called me in tears; I couldn’t believe it. My phone immediately began to buzz non-stop. She was cherished by many of us. Her memorial is bound to be a profound tribute.

Every communication from Jill held the possibility of an exciting escapade. I never declined her invitations. Whenever she proposed something, I understood that it would involve an adventure, so I always agreed, even during my pregnancy with my son.

Back in 2007, I embarked on an extraordinary journey alongside Jill when she tasked me to compose a song for Ariana Huffington’s book launch. The intriguing title of the book was Right is Wrong, which delved into the misguided tendencies of the right-wing politics. We crafted a song that mirrored this theme, featuring Ariana rapping at its core.

Incredibly, Ariana came to my home studio to record her rap part. The book release turned out to be nothing short of spectacular as we found ourselves on a private jet bound for Larry Ellison’s abode in San Francisco. There, we performed the song alongside Ariana in front of none other than Nancy Pelosi! Can you believe it? This all took place before Obama was even elected. Needless to say, that was one of my most unforgettable escapades with Jill. The likes of Larry David and his wife, as well as Nora Ephron, were also in attendance. It was a whirlwind of excitement, an exhilarating ride I’ll never forget.

Among many events, one that stands out is when we supported Bernie Sanders during his 2016 presidential campaign, specifically at an Iowa rally where we took on the persona of the “Sandrews Sisters.” We even composed a song about net neutrality. Whenever a promising opportunity arose, I would enthusiastically respond ‘let’s do it’, and Kay would join in too. On occasion, these collaborations led to unexpected performances, such as one in a billionaire’s home.

She never resorted to name-dropping or showy behavior. Instead, she rose above such trivial aspects associated with celebrity status. People admired her immensely, particularly Kara Swisher. She was influential yet not manipulative, often compared to a figurehead within the lesbian community or an inspiring muse for a political movement. She also had a knack for humorously criticizing the absurdities of the conservative right.

It’s truly disheartening to see so many people struggling during this political period, as we all anxiously await the midterms, hoping to navigate through without significantly compromising our democracy. Our excitement in collaborating with Jill was centered around finding a means to channel our fear and apprehension, and exploring the ironic and humorous aspects of the absurdity we’ve been experiencing. With her, the goal was always to find humor in the horrific. We were eagerly anticipating the writing process together. It’s only now that I realize we won’t be able to do that.

She was wonderfully unbound, a unique state that often leads to aimlessness for others. However, unlike being unhinged, she never veered off course. It was simply an exhilarating independence that seems elusive in today’s world. She embodied the essence of a free spirit. While she did have significant relationships and didn’t bear children, her inherent restlessness meant constant movement was part of her life. Her allure was palpable, and it wasn’t hard to see why people might feel a pang of envy for her unfettered freedom. Yet, there was no alternative path for her.

As a songwriter, she was both inspiring and contributed significantly. She served as a source of innovative ideas without being bossy or overpowering. She excelled at collaborating with others and was ideal because she didn’t criticize your ideas or stifle creativity. Instead, she was always supportive and had a consistent stream of ideas flowing. When we composed songs together, we weren’t aiming to create chart-topping hits. Rather, we had an objective: to write a humorous tune related to policy or politics. This task was never challenging; it was always effortless.

During much of my pregnancy with my son, we were often out on our adventures. She had met him when he was just a toddler, but didn’t know him as well as she knew me. Recently, when she visited a few weeks ago, we spent time writing together and she ended up staying longer. Upon returning home from school, my 17-year-old son encountered her work. They seemed to appreciate each other greatly. Since that day, he’s delved deep into her songwriting, particularly admiring tracks like Underdog Victorious and Mexican Wrestler. Being her friend, I didn’t fully realize the profound impact she was having on him at the time.

Her talent as a songwriter struck me anew; it’s so effortless to overlook when focusing on her friendship. Beneath her vibrant personality and humorous demeanor lies a songwriting genius that I fervently hope people rediscover, cherish, and truly acknowledge. She was nothing short of enchanting.

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2025-05-03 04:25