For my sophomore slump holiday card effort, I ricocheted from the bondage-heavy shock-jock scene of the first to a more somber and contemplative pose as seen below. As soon as the first card set up an element of expectation for the follow-up, I knew I’d have to do something entirely different rather than attempting something to top the untoppable. Cue this calm shot from a trip to the green hills of San Diego, as captured by my brother.

We were there for a family wedding, and that was the trip I first came out to my brother as gay. (He thought I was doing it to be trendy, and I don’t think I entirely convinced him it was true, but it did end up sticking.) Madonna’s ‘Evita’ was very much my influence and obsession at the time, so I quoted her on it via Eva Peron: “So share my glory, so share my coffin.” Once again, it sparked whispers of suicide, which were slightly more understandable given the quote, and at that stage of my life I fervently believed that whispers of anything were better than no whispers at all.

This one remains a favorite in the entire canon of cards, mostly because it’s such an incongruous setting and background. I still remember that sunny day in San Diego – my brother and I were hanging out and he showed me to a vintage shop where I picked up the feather boa used in the featured shot above. Then we walked about in this rolling grass field, an impossibly beautiful day in late November for the Ilagan brothers, who had come from the already-frigid and wintry Northeast. It lent this holiday card an element of warmth that was missing from the first year. It also set the stage for the possibility of surprise through understatement – a trick that would come to define ways out of other creative conundrums. Every time the world expected me to zig, I would choose to zag. Coupled with the first card I did, this one was my way of showing my yang after having already given up my yin.

For one of my very first acts as a twenty-year-old adult on his own in Boston, I decided to take part in one of the most grown-up traditions I could think of: sending out Christmas cards. Such a tried and true tradition also reeked of dullness and banality, which I took as the ultimate challenge. Of course I’d been writing Christmas cards to my friends for years – sometimes finding unique ones that didn’t have Santa or Christmas trees or glitter on them. (The only time I didn’t fancy glitter was on a Christmas card because that’s where one expects it to be.)

When I was a kid, my Mom’s friend had sewn an adorable bear that we hung on the door in our entryway, extending its stuffed arms to hold a basket made for holiday cards. I thought it was the greatest thing – a creation that celebrated crafting and letter-writing and Christmas spirit. It held the usual red, green and gold cards from neighbors and relatives and family friends, but it was the bear that was the most interesting thing about the Christmas card tradition. I aimed to be more exciting than that bear, and any of the cards it held in its cozy arms.

My holiday card would have to stand apart if it was ever going to be the focal point of any card display, and my initial goal was to the make it onto the family fridge of all my friends’ houses, and maybe, eventually, if I did it extra right, to be deliberately left off of the family fridge certain years for being too much.

That first year, however, I played it relatively safe. Earlier in the summer, channeling Madonna’s ‘Human Nature’ video, I’d done a basement photo shoot in shiny latex and a leather collar, a dog chain pulled taut (TAUT!) and a pair of handcuffs (an accessory from a Limited Edition of Madonna’s ‘Erotica’ album) doubling as a belt. This seemed a fitting first Christmas card, because nothing says Christmas like a touch of bondage and S&M.

It made the intended splash and set the slightly-surprising tone for all the cards to follow – even garnering some element of controversy when a friend’s father misinterpreted the image as a scene of me killing myself via hanging (when suicide was so 1992). It seemed a little shocking at the time – feels nostalgic and quaint by today’s standards.

Through the years, my holiday card became the one that certain people waited for and clamored to see – because who else bothered to put much creative effort into a Christmas card? To keep it enthralling to myself, I’d volley and vacillate between a shocking/provocative image one year, and a somber/serious one the next, exemplifying the extremes to which I sometimes felt drawn. More on that dichotomy in another post, as I managed to unearth the second card I did way back in 1996. The years between that and 2004, when I finally went digital (and kept better archives) have largely been lost to time and poor attic-filing retention. Everything from 2004 and beyond has been immortalized here (see below for the full list).

This year marks the 30th anniversary of my very first effort, and in honor of that I’m attempting to achieve a throwback to the shock and awe/aww/eww elements that the first card produced. It was also the hardest card I’ve ever shot, so trust men when I tell you I worked for it. Stay tuned… (and scroll down for previous cards!)

• 2004: The Snow Queen
• 2005: Disco Ball Shock Jock
• 2006: Christmas Crucifixion
• 2007: Bad Dumpster Santa
• 2008: Beautiful Christmas By the Sea
• 2009: Angelic Ass
• 2010: The Wedding Card
• 2011: Uncle Al’s Radio Flyer
• 2012: Eat Your Holiday Heart Out
• 2013: The Baby Brothers Ilagan
• 2014: Let It Snow
• 2015: A Holiday Ax to Grind
• 2016: Little Baby Jesus
• 2017: Classy Condo Cheers
• 2018: Incendiary Reflection
• 2019: Bake Me a Man
• 2020: A Family Affair
• 2021: Winter Slumber
• 2022: The Godfather
• 2023: Father Time
• 2024: Shitter’s Full