Singer/songwriter duo Tipps and Obermiller have affinities with Folk and Americana, but don’t set out with genre in mind when they write and tend to adapt sound to subject matter and inspiration. Their 2023 debut album, Love (and other mysteries), hailed from years of various musical gatherings from each songwriter, as well as three of their first co-writes together. Their second release in 2024, MacGuffin, was more sparse, allowing them room for more vocal collaboration and storytelling.
Now, we’re very pleased to premier the single and video for “Complicated Boxes” featuring Hilary Tipps today here at Wildfire Music + News. The song’s official release date is November 29th, 2024, and it has a close relationship, as part of a double single, with the song “Buckle Down.” It was Produced by Jana Pochop, who is also a prominent singer/songwriter in her own right and has become a Producer in recent years.
The song is decidedly a holiday-themed creation, but one that treads its own path in reassessing and exploring the experiences and associations we have with such an important time of year for many people. I might be tempted to call it an “anti-holiday song”, but that wouldn’t be fair, because I think the song in equal parts captures the sweetness of the writer’s holiday memories and deeply felt pain and disappointment that they still carry as a result of family disconnection around the holidays. That’s a remarkable achievement, something that’s accomplished both through the lyrics and instrumentation and brought to completion through Hilary Tipp’s very carefully measured vocals. We all love the uplifting, sometimes superficial but lovely holiday songs that reemerge every year, but one like “Complicated Boxes” that takes on personal struggle and suffering surrounding family relationships may the holiday song that many of us most need to hear.
The song uses the imagery surrounding gift-giving to literally and figuratively spell out the multi-edged relationship between the narrator and their parent, never quite managing to elicit the responses they were hoping for in the gifts they give. Probing deeper into the issue in hindsight, the speaker reaches some meaningful revelations about gestures of love and how they are received. The conclusion, that the two spoke different gestural languages, helps alleviate the depth of negative feelings surrounding the holidays caused by this distance, but doesn’t seek to rewrite history. The fact that the speaker, now finding themselves in their parent’s role, can admit that there’s a lack of conclusion to this story, is part of being real and facing the lessons that life has taught them.
The sound of the song is both gentle and emotive, with a degree of chiming precision that does remind of traditional holiday songs in a subtle way. It conveys the sweetness and warmth of many of the images in the song, drawing the audience in, then uses that confessional space to explore further. The video, which was directed by Shawnee Kilgore, makes for an excellent accompaniment, visually settling on many warm images of the holidays, as well as old family footage of togetherness, while continuing to direct attention back to the idea of gift-wrapping and the “complicated boxes” that can’t really contain the emotions the holidays create, whether radiant or painful.
Hilary Tipps shares a personal backstory for the new song:
This song is cells on a slide, pressed together and stained with hope that this finds a place in the milieu of holiday experience. My best and worst memories with my parents are around holidays. They are both gone now, and I am sorting. My mother was an accomplished psychologist, hobbled by her own unhealed trauma and Christmas was her favorite. The house became a masterpiece of Victorian mauve, flocking and tiny winter villages. She was extravagant and thoughtful in her gift-giving. However, one could, perhaps, search high and low for the most perfect and thoughtful thing, wrap it beautifully, have her do a fun scavenger hunt to find it and watch as she opened with hopeful expectation only to see her eyes drop and her politely whisper “thank you” because there was no way to get it right. She needed to receive love in the exact way that she gave it: an impossible riddle. Just a little song trying to get my arms around that.
About the Winter “Double” they are releasing, Tipps & Obermiller add:
When we initially made the decision to release ‘Complicated Boxes’ and ‘Buckle Down’ as Winter “doubles” (as we call them), we wanted to run the experiment of having someone each take on the full reigns of production with our work. Our previous recordings have been a mixture of self-produced with some production help from others that just included talking about overall instrumentation for the projects. Looking towards the future, we wanted to have the experience of listening to established voices for the visions of our songs, and working with them to create something we have never done before.
We chose artist and producer Jana Pochop to produce ‘Complicated Boxes’ for her ability to weave dreamy soundscapes through a song. This fit perfectly with this melancholy Christmas tune.
As for ‘Buckle Down’, Steve went down to producer, engineer and multi-instrumentalist Taylor Tatsch’s studio for a day. Taylor has produced some of our favorite records, and we knew his ideas would take this song to new heights.
We are so grateful for Jana and Taylor’s stellar work to make these songs into the beautiful creations you hear today.
The song “Complicated Boxes” was written by Hilary Tipps (music and lyrics) and Steve Obermiller (music), and performed by Tipps and Obermiller, with Production and instrumentation by Jana Pochop.

Lyrics:
Rain pours sideways in
The place where cars have always been
These Christmas cartons lost their fight with time
Torn open once again faint smell of cinnamon
Lonesome glitter, tangled tree skirt fringe
The garland and the lights go up
Wrapping paper over plastic stuff
It’s how I learned to box up all my love
Complicated boxes can’t contain their contents
The day that Christ was born
You were first up in the morning
Coffee and sweet rolls opening bedroom doors
So proud of what you gave. All the hurt to erase
But the gifts I give you don’t amount to much
When you open them up, the letdown comes
It’s how I learned to box up all my love
Complicated boxes can’t contain their contents
Heart shaped fears tucked deep within
You’ll never know when you’ll need them again
Now I’m the first awake
Sweet rolls in to bake
I close the door and take you from the shelf
I miss you a lot. There’s just this haunted box
Maybe next year I’ll return this dust
I’m sorry there were not enough boxes you could open up
To ever make you feel all of my love
Complicated boxes can’t contain their contents
Complicated boxes

