**From the desk of Jessie Howe**

***Written May 6th, 2024, after an epic weekend Reunion!***

Listen to the full article through the link below:

I just had one of the most epic weekends ever! This past Friday and Saturday was The Diggity’s Reunion & Benefit Show, and it was so wonderful that I feel compelled to immortalize the experience here as a sparkling chapter of a long and winding musical journey. Many people traveled, some from across the country, to come together and help raise funds for our wonderful friend Ian, who has been battling cancer. Ian has been with this band as a dear friend, manager, and supporter since my earliest days of meeting them. I am so happy to share that everyone’s collective efforts raised a good amount of money to help with medical expenses, and things are now going in a much better direction for Ian! This was one of the best events I’ve ever been invited to be a part of. My heart is so full of joy and gratitude for everyone in the universe of The Diggity, and the legacy of music created across their wondrous musical evolution. I’m pretty sure the vibration of the planet was raised by at least a few degrees from these shows!

In the following journal, I’m excited to delve into the history of how I met The Diggity, and how my time with this band has expanded and elevated my life (musically and beyond). I’ve met some of the best people I’ve ever known because of them, and am looking forward to sharing this story–especially for those who haven’t heard their music yet. I’ll include links to their albums at the end, which are available to stream on Spotify and Bandcamp.

For those who are unfamiliar, The Diggity is an incredible band that I had the privilege of playing with between 2009 and 2011, during my early 20s when I was working and saving money to go back to school. The original core members who I joined in this time period are Jake (lead vocals/guitar/effects/lots of things!); Alex (guitar); Marko (bass guitar), Vaso (percussion), and Eric (drums). Everyone jumped in on collaborative vocals and different sounds for different songs–this band knows no limitations (guys, I’m sorry if I missed anything!). They are truly among the finest musicians and best people that I’ve ever had the opportunity to play music with. We recorded an album together in 2011 that featured some of the songs we’d written during my time with them, titled ‘Another Wondrous Conversation.’ To this day it is some of my favorite music I’ve ever recorded, from the writing process to the final mix. On the album, I played piano/keys/organ, flute, backing vocals, and effects on a mini Korg across four of the tracks. This album is one of my favorites ever because it encapsulates a transition between the music I worked on with them and the fantastic musicians who followed me–it’s a great example of the vast sonic tapestry and musical openness that is the heart of this band.

Before I go too far ahead, I think it’s worth it to go back to the origins of how I met The Diggity, and how the experience of playing music with them opened my musical world. When I meet people at shows, events, and occasionally auditions, they often ask, “Where did you come from?” This is a great space to share my own journey of what I describe as sonic imagination, and the path where the expression of that internal life has led me.

Ever since I was a kid, I’ve always gravitated towards and LOVED music! From making up songs while playing in the woods to following along to my Mom’s piano, it’s always been a vibrant part of my life. I cherish that I had a childhood deeply intertwined with nature, because I think the development of a sonic imagination originates from learning to listen. Growing up in a remote place surrounded by forests, fields, and creeks, I was able to tune in to the music of the earth and internalize those sounds like a landscape. I especially loved becoming immersed in the sounds of evening—I remember watching the moon rise over our backyard as the chirping chorus of the natural world echoed, shimmering across the twilight sky.

Piano is my foundational instrument, after the one we all begin with–the human voice. Learning piano was a wonderful way to develop my ability to process through listening, and provided literal keys to unlock the melodies I wanted to express from within. I’ve always had an easier time learning music by ear with piano. When I was a little older, I started learning flute, and played in every part of Band up to my high school graduation. The approach to my learning flute was much more visual, as sight reading was an emphasized skill in my classes. To this day I usually keep little notes around when I’m writing melodies for flute, because seeing those notes helps me feel more confident in what I’m playing.

As I was learning to play different instruments, I remember listening to blues and funk music with my dad, 1970s folk and rock albums with my mom, and eventually followed my own interests into the music of cultures from around the world. Music with roots in Ireland and India deeply resonated with me. Soundtracks were always a big part of what I loved listening to, as well. I’m very drawn to musical storytelling. I’ve always had a kaleidoscope of influences, and while that has been a gift as a songwriter, it also made it difficult for me to find a “niche” in the genre-focused industry side of the music world. Playing music with The Diggity was the first group where I didn’t feel boxed in or limited in scope as a musical artist.

The road to meeting The Diggity emerged through a deeply painful, tumultuous time in my personal life. My initial connection point was an ex, who also played piano and was gigging with The Diggity off and on for a brief time. I loved going to their shows–I just wish I would have found them through a better person. This particular ex met me through one of the most difficult times in my life at that stage. My mom had become incredibly sick right after I graduated high school, and I had to leave college after the first year until I could afford to go back on my own. I was living alone in a small studio apartment, working multiple food service jobs and doing art commissions on the side. He was considerably older than me, and there was a lot to that situation that was extremely unhealthy. This relationship unfolded from when I was nineteen to just after I turned twenty-one. It was a deeply manipulative, narcissistic age-gap dynamic, and I didn’t know how to see it at the time because I was so emotionally vulnerable. The worst thing this particular ex did was go out of his way to try to diminish the light of my talent, and make me doubt myself as an artist. To my dear artists and friends: If a partner ever does that to you, especially in an effort to build themselves up–do not listen. They are threatened by your ability, and full of shit. Eventually, I was able to see through it all and rebuild myself from the inside out.

I did meet the love of my life (love you, Brian!) through the ending of that situation, and moved on to a much better place by the time I turned twenty-two. But, the amount of emotional turmoil I had gone through needed a way to be channeled outward–and that was when I wrote and recorded my first album. It was titled ‘Beyond the Burning Eye of Heaven:’ a sixteen-track solo record that I wrote and recorded out of my apartment, around my shifts at work. Writing that album liberated me–it was deeply healing, and helped me overcome the damage that had happened in those previous few years. By giving voice to it all, I was able to release it and move forward into a new chapter. This is one example of many where music has been my lifeline, as an artist and a human being. Looking back, the best way I can summarize it all is that sometimes, our darkest nights lead to our brightest days.

After I recorded that first album, I was really missing playing music with people. I’d become pretty isolated that year, during the entirety of the healing process. I went to a Diggity show in late 2008, and gave them a copy of my album. I asked if they’d ever want to meet up to jam or collaborate on a project, because I loved their music and they seemed like genuinely wonderful people. And, I really wanted to learn how to improvise more on keys! They were so receptive and positive to the possibility of working with me that I almost couldn’t believe it. I cried happy tears that night because it reminded me that there are infinite possibilities out there, and goodness in the world. I actually almost didn’t ask them, because I was so unsure of how they’d react. I don’t know if many of you remember the music culture in the early to mid 2000s, but it was not the best climate for women in music. I remember a LOT of ego flying around, and people putting down the work I did before they even heard it because it was written by “a girl.” I want to be super clear that not everyone was like that–but it was a constant struggle, and it’s a relief to see that those stigmas have loosened considerably since that time. One of the things that really stands out to me about The Diggity from those early days is that they never, ever treated me as less. I always felt very cared for and respected by them, and it’s because of those qualities that I was able to come out of my shell a bit and be more experimental with music. They gave me a place where I felt safe, and free to be myself.

I joined The Diggity for practice a few times at Jake’s place following that show, and it was so much fun! I had done some work with other rock bands throughout high school, but this felt different–it was broader in scope and musical possibility. I’d never really listened to much jam music before I met them, but I quickly fell in love with it. Somewhere, I still have the stack of CDs they burned for me to help catch me up to their influences. One day at practice (to my great surprise), they invited me to join the band. I was floored–I honestly didn’t expect it. They had told me they’d been looking for a keyboard player, as the original member had recently left. He had played keys on their first album, ‘Out of the Woodwork.’ My first thoughts were “Yes!”, and then, “Oh wow, I hope I can do this.” Because I felt so supported by them, I had this inherent trust that I just had to try. And I’m so glad I did.

I have so many beloved, wonderful memories from the period of time when we were writing, practicing, and playing shows together. Writing my first solo album taught me how to process and emerge from heartbreak, and the music I created with The Diggity taught me how to embrace light and laughter in sound. Initially, I had a lot of stage fright to get over. But with experience, it became more second nature to be on stage and I really had fun at our shows! That was possible for me because of the inclusive environment the guys created, as well as every incredible person who supported the band. I’m at a place in my life now where I genuinely enjoy performing onstage, but where I still feel the strongest is in the writing and recording process. The energy of writing music with people is unlike anything else–it’s a magical synergy that emerges and transports you. And when you feel it–really feel it come together collectively–it’s one of the best experiences in the world. Being able to share that work with people and bring joy through a show is the next level of awesome. I was playing with The Diggity just long enough to experience that full cycle and really appreciate it, to the core of my being.

The only downside I remember from this era is that I was surviving on a very low income, and working full time around our practices and shows. I had made a promise to myself that I would go back to school when I was able to. At the time, I had to wait until I was at least 24 years old, to be considered an independent student and eligible for financial aid. I was working late nights and early mornings as a baker for Panera Bread. For the most part, the schedule worked around our gigs–but it was physically strenuous and I remember struggling to balance it. I was constantly worried that I was holding the band back. Because of my work schedule, I wasn’t able to take last minute shows when they were offered to us. And I couldn’t risk calling off and getting fired because I had no financial support system to fall back on. Looking back, I do wish that I would have called off a little more–it wasn’t actually as big of a deal as it seemed back then. But what I can say with full conviction is that every late night and early morning was worth it. I wouldn’t trade the time I had with The Diggity for anything, and they helped me musically and artistically more than I could ever tell them.

In late 2010, I had to make the extremely tough decision to leave the band. It was heartbreaking, and I think they knew. I was finally able to start applying for schools again, and even though I saw a future of possibilities with The Diggity, I knew that it would eat away at me forever if I didn’t keep that promise to myself to finish my education. I had a very narrow window to apply for scholarships and explore those possibilities due to different age requirements. It’s absolutely true that you can always go back to school–but certain options for financial aid are not always going to be there. Jake actually brought it up before I could find the words, and we had a really good conversation about it. He told me something that I’ve never forgotten, and still try to live up to: “Great art cannot be great art if it’s never seen.” It’s a truth I try to remind myself of when I catch myself pulling back too far behind the scenes. There’s so much art living within each of us, all the time–more than we may be able to put out in the world. But, it’s the effort we make on that journey that matters. I made a commitment to myself after that conversation that I would never give up on music, art, or myself–and I never have.

There was a window of time in the winter and spring going into 2011, which is when The Diggity invited me to record some of our songs on their new album. I was elated that they asked me to be a part of it! I wasn’t starting school until the fall semester, and it was a great opportunity to record the music I was the most proud of from our time creating together. This was the making of ‘Another Wondrous Conversation.’ It’s still one of the most enjoyable, fun creative processes I’ve ever experienced in recording music. I remember the backroad drives I’d take out at night to this big farmhouse in Lowell under a glittering night sky, where a sound engineer had created a home recording studio. I’m trying to remember his name, but I clearly remember his face and how awesome he was. The quality of that recording, especially for technology available at that time, was outstanding. I felt so at ease and free to have fun, and it brought out the absolute best in me as a musician. The other amazing thing about it is I had the chance to meet Kevin, a fantastic musician and MC who became the newest member of The Diggity after I left. I can’t imagine a better person to come in–the creativity and texture of sound that he brought diversified and expanded The Diggity’s music in the coolest way! I remember what a joy it was to hear some of the new songs and spend time with them all. It also gave me some much-needed emotional closure that they were going to be more than ok in this next era of their musical journey. Because of the creation of that album, I have the best record of a spectacular period of my life. That is a priceless gift.

After the album was released, I had some choices before me with what to go back to school for. The two main paths I was exploring were Theater Design for the stage, and Music for Visual Media. What eventually helped me decide was the realization that music is the deepest, most personal channel of art that I create. I didn’t want the grind of a full degree to diminish that light or overly structure my creative process, which I feel extremely protective of. I had to choose what would be best for the evolution of my own sonic imagination. There was more flexibility to take music classes under the umbrella of a Theater Design degree, so that is ultimately the path that I chose. It’s also where I had the most opportunity to learn new skills. I majored in Scenic Design and minored in Sound Design at Columbia College Chicago, and saw that path through to my graduation in 2016. I really enjoyed my theater and art classes–but some of my absolute favorites were in musicology, sound, and art history. Everything I learned are skills I actively use today, and I do feel like I made the right decision. It’s an impossible heartbreak, to love two things so much that you can’t hold simultaneously. Even with that restriction, I still found many ways to create space for music in my life during school, and it helped me work through a lot of challenges. I remember going to the Sherwood Music Center off Michigan Avenue, which was pretty close to the old design building. I could check out a practice room using my student ID, and it became my refuge on the longest of days. There were a multitude of rooms filled with the expanse of grand pianos, it was an amazing resource to access. I also recorded some of my compositions for sound designs in those practice rooms. Even when I was weeks-deep into designing, building, and painting a show, music was never far from me. It’s something I’ve always kept alive within me.

As years progressed, The Diggity continued to evolve musically and release new songs. They had two amazing vocalists join, Shelbi and Leah, and that transformed their sound so beautifully! I fell out of touch with everyone during those insanely busy years while I was at school, but I kept checking in with their music and listening. I’d put on their albums when I needed to uplift my spirits and remember why I create art. It kept me going through a lot! Especially in those first years working in Chicago theater. I worked a lot of late nights and long hours, painting/building and designing shows across the city. The Diggity would be with me on the frigid winter walks through downtown alleys, early morning drives home as the sun was rising over the glimmering lake, and countless midnight hours spent painting for miles on stage floors. A lot of people knew me as the singing scenic painter, because I always had music going when I worked. I listened to The Diggity when I was recovering from my first serious injury from work, after I shattered my collarbone falling off of a stage. I would also listen to them on happier occasions when I’d be on walks in the evening and unwinding from the day. On my adventures traveling to other countries, I listened to The Diggity on the plane while I wrote out the dreams of every place I hoped to see. Even when we didn’t see or talk to each other for years, because of music, they were always present in my heart.

So now that you have the backstory…allow me to catch you up to recent events! Across the past few years, I’ve transitioned to doing theater design and scenic painting contracts part-time, and now have a small art and crystal business that I do markets for. Many of you reading this may know me because of our market booth. I absolutely love creating art and being a vendor! The people that this shift has connected me to are absolutely amazing, and I feel like I’m in a much better place with my work balance. In February, I had a booth set up at the first-ever Journeyman Artisan Market at their new Valparaiso location. And while I was there, I saw Sarah! A beloved friend from The Diggity days. We spent some time catching up as her son looked through the many crystals and fossils in our booth. Sarah told me that our friend Ian had been battling cancer, and that there was interest in organizing a benefit for him. They were thinking about a reunion show in May, but didn’t have anything confirmed yet. My heart lit up when she told me this and I offered to help in any way I could.

Shortly after the market, Vaso sent a message asking if I’d be interested in being a vendor at the reunion show, and possibly playing a song with them. It was an instant yes for me! I was so beyond excited that this was really happening, and wouldn’t miss it for the world. Especially because it was going to help Ian. As details were confirmed and planning began for this reunion benefit, The Diggity reached out to see if I’d like to play Muffin House 2 (a song from the album we recorded), and possibly the flute solo on ‘Bulunda.’ Those are two of my favorite songs we played, and it was a definite yes. But…Muffin House 2 is an 8 + minute epic jam, and it’s been a while since I improvised an organ solo. I started practicing in the windows of time I could carve out around work for our small business and paint contracts. Many wonderful midnights were spent in my music studio at home, remembering the different syncopations and styles of music from The Diggity days. I decided to write out what essentially became a four-page map of the song, because it has a number of different sections and I wanted to memorize the order correctly. I hadn’t played this in twelve years, but that didn’t even matter because I couldn’t wait to see everybody.

We eventually arrived at the week of May 4th. Everyone was coming into town, and most fortunately, there would be a band practice. They asked if I could come to the practice on Thursday night. Originally there was only one show on Saturday, but tickets sold out so quickly that a second show was added on Friday night. Excellent news! But I think we all felt an extra bit of pressure from the overwhelming interest, and we all wanted it to be great. I’m not sure how much time had passed since The Diggity had played a show together, but I know it had been a number of years. I was so excited to see everybody that it eclipsed any nerves I would have had. At this stage in my life, I want to cherish, celebrate, and enjoy these moments when they happen, and nothing was going to keep me from embracing that.

When I arrived at the Banta Center, I was a little worried I would be late–naturally, I was stuck behind a train on the drive in and running about ten minutes behind. When I pulled up, I saw everybody standing on the lawn and staring up at the window. It was amazing and surreal to see everyone together, I was overwhelmed in the best way! What was happening is they had all accidentally been locked out of the building, and the one person who was inside was playing drums, oblivious to the shouting from below. Hilarious, and brings back memories!
Eventually we all got in. I had never actually brought the keyboard I now have out for a show, since I’ve been doing all of my recording and music work from home. I love this keyboard, it’s a full 88-key Roland–I had it wrapped snugly in a giant bedsheet, with my pedal and cables in a small bin. And I brought my questionably sturdy keyboard stand that probably needs replaced soon. It worked though, and after heading up the stairs with my gear, I was in a room with every member of The Diggity. It was wild, surreal, and absolutely wonderful. I LOVED band practice! The energy, the sound–it felt amazing. I was a little nervous to jump into playing Muffin House 2, but once we started going, it came back. I felt my heart wake up–it’s like recalling a part of yourself that hasn’t felt sunlight in a while, that only emerges in a specific time and place. It was just as awesome to hear all of the wonderful music they’ve created in the many years since I left the band. I went home in a state of complete and total joy that night.

Then, the marathon weekend began. The Diggity Reunion Benefit fell on either end of the opening day of Chesterton’s European Market, which is our main home for the market season. We couldn’t miss opening day–but there was no way I was going to miss the Diggity Reunion, either. I had an indoor set up planned for the Diggity Show, and a separate display for our tent at the European Market. I had my music gear stashed at my office in downtown Valparaiso. I was as prepared as I could possibly be. Once I had transported everything to the venue and set up, I felt a wave of relief and had a blast listening to the opening bands. My youngest brother, Sean, and my Dad came out to help with the booth and enjoy the Friday show! I played flute on Bulunda for the first night, and it was SO MUCH FUN! The energy of the crowd was electric, and a great show was had by all. The whole experience reminded me of how much happiness live music has always brought into my life. This was a reunion of the best kind–the joy of seeing people I haven’t crossed paths with in years, of meeting their children and hearing stories about their lives–it’s truly incredible.

I squeezed in a couple of hours of sleep before it was time to load in at Chesterton on Saturday morning. The opening day market was phenomenal! We had such a fantastic turn out, and this felt like a second reunion–we saw many incredible friends we’ve met through our market booth and our business. This is where the coffee and adrenaline kick in and become my superpower. I remember feeling the pain in my feet, but aside from that, I was holding up pretty well. Brian and I finished out the day at the European Market feeling exhausted but uplifted, and accomplished. We found the energy to keep going and loaded our cars together. Then, I picked up food, headed home, changed clothes, and reset my mind for the second show. This is the one where I’d be joining them on keys and flute, and I wanted to be as prepared as I could be. Because Muffin House 2 had gone so well at practice, we only ran it once. As I drove to the venue it dawned on me that I was about to perform a song over 8 minutes long for a sold out show, and had only played it with the band once in the last twelve-plus years. Without much sleep to go on. But you know? These are the moments where one can harness what I call “performer energy.” It’s the confidence, conviction, and slight absurdity that must be conjured to navigate such things. This is exactly where all of those high-pressure situations in theater work have conditioned me to be strong and trust myself. In full honesty, the nerves were there, but I wasn’t going to let it stop me from enjoying this extremely special, unique opportunity to play music with people I love.

I’m happy I was unaware of the camera that my dear friend Karl was orchestrating to record the event, because if I had paid any attention to it, that might have thrown me off. I’m so glad he did all of this work to film the show, though! It’s going to be wonderful to have a recording of the night, because Saturday was pure magic. The brilliant energy, the love you could feel in that room–it was absolutely astounding. I had a great time seeing it from two perspectives, both behind the crowd and onstage. Sharing this time with my younger brother was also incredibly special. I don’t know how I could have done it without him, so I’m extremely grateful that he was free that night and able to run our booth. I honestly have no way to gage how I did onstage, but I had a lot of fun! It was like a surreal, beautiful dream–just being up there behind a keyboard, seeing The Diggity across the stage, and a thriving crowd surrounding us. Extreme sensory overload in the best way, and transcendent joy is how I can describe the feeling. And I would do it again in a heartbeat.

I am so deeply thankful for the opportunity to have been a part of this, and to see everyone again. I hugged everybody, I cried happy tears every night, and I felt reminded of the immeasurable power of art and music. I’m in awe of the way these forces bring people together, and profoundly generate good in the world. There’s a part of me internally that feels more awake now, and I’m not entirely sure how to describe it. It was so incredible to see everyone and learn about the different paths their lives have taken, to meet their families and loved ones and hear about their journeys. Through it all we have this thing, this musical universe that connects us. My overwhelming feeling after leaving was a wish for everybody to be happy, healthy, supported, and inspired. I don’t know when I’ll see everyone again, but my God am I grateful that I had the chance to. In the meantime, there is art to create and music to celebrate. And I couldn’t be happier for that.

The Diggity: Discography

Available on SPOTIFY and BANDCAMP

Pumphouse (2015)

Halloween ‘14 (recorded live in 2014, released in 2015)

Human Skills (2012)

Another Wondrous Conversation (2011)

Out of the Woodwork (2007)

The Diggity: Official Facebook Page

The songs I am on from Another Wondrous Conversation are: Muffin House (piano/keys/effects); Peatin Eopleup (piano/keys/effects); Bulunda (flute); and Muffin House Pt. 2 (organ/keys/backing vocals).

Throwback Memories and Moments from this Week: