LITM Singer-Songwriter Picks Featuring Jackie Conn, The Kentucky Trust Fund and more!

This edition of LITM Singer-Songwriter Picks will surprise you with its lilting tones and intimate setups, featuring artists The Kentucky Trust Fund, Eric Osterhout, Maria Mihailik, Audra Watt and Jackie Conn

1. The Kentucky Trust Fund – I’m Coming Back

A song that takes you through the landscapes of the Appalachian terrain with its rustic touches of mandolin and earthy crunches, ‘I’m Coming Back’ is wildly catchy. It features a rhythm that draws you in alongside free-roaming vocals that feel untethered by the general flow of the song. There’s an endearing duo of leading lines drawn by the instrumental section and Sarah Houck’s singing. The track starts with earthy, tactile clinks of percussion and Houck’s pristine vocals, followed by a delightful mandolin solo that reappears toward the end. Overall, it's an endearing track worth adding to your Bluegrass and Americana playlists.

2. Eric Osterhout – The Stillness Before the Rain

Another great outdoorsy track with almost Wordsworthian lyrics is Eric Osterhout’s gentle piece, ‘The Stillness Before the Rain’. The song sits in the cosy corners of the Country/Americana genre, using a glistening set of synth notes alongside vocals that ooze nostalgia. With “Sittin’ on the tailgate watching clouds roll in…” the track has an intriguing opener that sets the tone as the vocalist steps into storyteller mode, guiding you through a calm landscape right before the storm breaks. The instrumentation feels like an exercise in mindfulness, making it a great track to sink into.

3. Maria Mihailik – Mary

A vocal-driven track, ‘Mary’ is a soulful ballad that renders a soft, intimate layer of melody onto a light, atmospheric underbed. Mihailik’s vocals are carefully placed, with a heartstring-tugging vibrato that drifts into a powerful, yet controlled quiver. The track begins with only a few hints of instrumentation before the vocals take over; when the full arrangement joins, it ties the whole composition together. The bass acts as a grounding force—a subtle presence that adds to the quiet emotional weight of the piece.

4. Audra Watt – I’m Not Sorry

Audra Watt’s latest track is somewhat of a Gen Z anthem, defined by her unapologetic tone and lyrics. The song is a quiet embrace of humanity with all its flaws, where the artist’s approach is a polite assertion rather than a loud, anthemic release. The resulting message feels warm and approachable, removing any cynical element typically associated with the theme. This is hammered home with lyrics like “I’m the Duchess of daydreaming” and “for the first time, I’m not sorry.” The instrumentation reflects the welcoming tone of the vocals, offering an atmospheric vibe that perfectly matches Watt’s velvety delivery.

5. Jackie Conn – Baking Day

‘Baking Day’ encapsulates all of Jackie Conn’s core memories and nostalgia in one endearingly uncomplicated and tender song. The lyrics are delightfully charming and poetic, with each line acting as a short story from the artist's life, such as: “And it’s Sunday with my mother in the kitchen baking cakes.” The soft background tones of the instrumentation add to the poetry of the scene, featuring brushes of chord arpeggiation and subtly bright, airy notes. Conn’s vocals are satisfyingly gentle, with the mix maintaining her timbre of dewy, honeyed vocals. Overall, it is a uniquely and carefully crafted song that stays with you long after it ends.

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Source: LITM Singer-Songwriter Picks Featuring Jackie Conn, The Kentucky Trust Fund and more!