I have to give all the credit to my friend Kelly for this one. My friends come up with such fun projects for me to do, and this one was AMAZING.
If you’re painting your own advent calendar this year, or just looking for ideas for pop culture Christmas paintings, scroll down to see images from my three advent calendars and tips from me! Happy crafting!
Way back in 2020–The Year That Shall Otherwise Not Be Named–Kelly texted me and asked if I could paint something for her.
She had bought an unfinished wooden organizer, and hoped I could turn it into an advent calendar for their family.
Um, first, YES. I love Christmas. I love Christmas movies. I love painting movie references and little details. So a thousand times, YES.
Second, I was a little scared I couldn’t pull it off, but that’s how I always am when my wonderful friends put so much more faith in me than I have in myself. I am SO glad Kelly trusted me with this!
It ended up being a huge undertaking, but such fun to paint tiny little details. I think I love tiny paintings!
Here’s what Kelly requested:
- Favorite movies: Frozen, Love Actually, It’s a Wonderful Life, Harry Potter, White Christmas, Elf
- Favorite carols: “I Want a Hippopotamus for Christmas,” “We Three Kings”
- Various Christmas images: gift wrap, a tree, a mantel, anything else to fill up space
And here’s what I came up with (key included below the picture):

1 – Green and gold gift wrap
2 – “To me, you are perfect” – Love Actually
3 – Christmas Tree
4 – Olaf
5 – Snowflakes
6 – Christmas Bell / Clarence’s Bell from It’s a Wonderful Life
7 – Vintage ornament
8 – Natalie’s door – Love Actually
9 – Christmas Mantel
10 – Ron and Harry’s sweaters
11 – Vintage ornament
12 & 14 – Combo scene: We Three Kings
13 – Zuzu’s petals – It’s a Wonderful Life
15 – White Christmas
16 & 17 – various Christmas garlands
18 & 19 – Combo scene: falling snow / Vermont in White Christmas
20 & 21 – various Christmas gift wrap
22 – “I Want a Hippopotamus for Christmas” carol
23 & 24 – Combo scene: Buddy the Elf saying “Santa! I know him!”
I loved this so much that I made one for our family as soon as my usual holiday rush was over.
Here’s my family advent calendar (key to follow):

1 – Grinch’s heart breaking the meter
2 – Wreath
3 – Scrooge’s door
4 – Elsa – Frozen
5 – Zuzu’s petals
6 – John McClane – Die Hard
7 – Natalie, David, and the Octopus – Love Actually
8 – Lights from Stranger Things
9 – Shitter’s Full – Christmas Vacation
10 – Ron and Harry’s Christmas Sweaters
11 – Who Christmas – Grinch
12 & 14 – Combo snow scene; Vermont
13 – “Sisters” – White Christmas
15 – Billy Mack and Dancers – Love Actually
16 – Vintage ornament
17 – Kevin McAlister screaming – Home Alone
18 & 19 – George Bailey lassoes the moon – It’s a Wonderful Life
20 – Garland
21 – Buddy the Elf
22 – Star of Bethlehem (combo with 24)
23 – Elevator buttons from Serendipity
24 – Nativity scene
But wait! There’s more!
One of my long-time followers and an Insta-friend asked if I could make one for her the following year. I was pregnant at the time, so this ended up taking a little longer than usual because of unexpected pregnancy fatigue (having a baby at 35 is exhausting!). But I got this mailed and shipped to her just in time for the 2021 Advent season!
Here’s The Annie, with key to follow:

1 – Grinch
2- Hermey the Dentist Elf from Rudolph
3 – Rudolph
4 – gift wrapped box
5 – snowflakes
6, 12 – Elsa’s castle
7 – “To Me, Your Are Perfect” sign from Love Actually (she requested that 7 goes in this spot)
8 – Natalie, David, and the Octopus – Love Actually
9 – Shitter’s Full – National Lampoon’s Christmas Vacation
10 – Ron and Harry’s Christmas sweaters
11 – Christmas ornaments
13 – Whos singing from The Grinch book
14 – Journey from Jingle Jangle
15 – Nightmare Before Christmas
16, 22 – Snowy holiday scene
17, 23 – Buddy the Elf shouting “Santa! I know him!”
18 – Pine tree
19 – Max from The Grinch
20 – Marv and Larry from Home Alone
21 – an envelope from the movie Klaus
24 – nativity scene
With Annie’s, you can tell that I practiced painting a lot more in 2021. My paintings were SO much better on hers!


This is such a fun project to take on, and if you’re artsy, I highly suggest you try it! It’ll take a while (Kelly’s took a week where I was entirely devoted to it; mine and Annie’s took a month because I had other projects and obligations), but I think it’s so worth it!
Here are my tips if you decide to take this on:
Search for a wooden organizer with drawers that has unfinished wood. I used the Hyggehaus from Amazon (not an affiliate link) for all of mine, but there was a weird little period when it was out of stock. If you have to do another style, make sure you pick unfinished/raw/nude wood.
Gesso first if you can. At the time that I painted these, I did not use gesso as part of my wood painting practice. Now I do, and I can tell the difference. The advantage of gesso: the paint colors pop much easier, with fewer coats required. The disadvantage of gesso: your project takes longer, and it covers up the wood grain.
My supply list: I painted everything in basic acrylic paint. I added details with Posca 0.7mm paint pens in black and white, then added shimmery details with DecoArt Liquid Gold and Liquid Silver extra fine pens. If I could do this over again, I would varnish everything before I did my metallic details. But varnish takes away the shimmer from the DecoArt pens, so I can’t do it to mine without taking that away!
Sketch it out first. I used Procreate to do a mockup and plan out all my images. This helped me see which ones were realistic and not, and see how color balanced in the whole piece. Below is the draft I made for Annie (notes in the margins are the images she requested. I crossed them out as I figured out places to put them.)

Build in some combo drawers in your design. Some of my favorite parts of these are the ones were multiple drawers are in dialogue with each other. I love that it makes a larger piece, and it also allowed me to not have to paint such itty bitty, teeny tiny details.

Commit to a long time to complete this, and enjoy! I loved watching Christmas movies, snacking, and wining while I made mine. Taking on big projects like this is a combination of relaxation and creative exercise for me. At times, I was overwhelmed with how big the project was, but in the end I was SO proud! I am still proud every time I bring this out.
I hope you enjoy this project! Let me know how it goes!
