Choosing Joy

Actor, singer, dancer, and all-around multi-hyphenate Trevor Jackson joins Holiday AF for a joyful, hilarious, and heartfelt conversation with hosts Deborah Joy Winans Williams and MAJOR.. Born in snowy Indianapolis and raised in sunny Burbank, Trevor reflects on growing up between two worlds — from blizzard-filled Midwestern Christmases to laid-back California holidays.

Trevor shares childhood stories of walking miles through icy Indiana winters, the traditions his family still holds dear at his grandmother’s home, and why returning to loved ones feels like “plugging the iPhone back in.” He also reveals his dream Christmas destination (Hawaii), what snow he’s not trying to see anymore, and how he keeps gratitude at the center of the season.

The Holiday AF “Finish the Lyric” game brings out Trevor’s comedic side as he belts out classics like “Silent Night,” “Joy to the World,” and “Santa Claus Is Coming to Town,” while the hosts challenge his memory and vocal dexterity. The episode closes with laughs, chocolate tasting chaos, and warm holiday wishes.

This episode blends nostalgia, humor, talent, and holiday spirit — everything that makes Trevor Jackson a fan favorite.

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Actress and activist Logan Browning joins Holiday AF for an inspiring, heartfelt, and joy-filled conversation with hosts Deborah Joy Winans Williams and MAJOR.. Known for her breakout role in Netflix’s Dear White People, Logan opens up about the artistry, activism, and family values that shaped her — and why her holiday traditions remain so important today.

She reflects on growing up in a home overflowing with love, people, and generosity — the kind of Christmas where everyone who walked through the door received a gift. Logan shares how her parents created unforgettable holidays, why their house was always full of guests sleeping on couches and floors, and how those traditions have evolved into adult life with white elephant exchanges and name-picking gift rituals.

The conversation dives into her views on social justice, the artists who influenced her, and how the arts became her earliest form of activism. Then comes the rapid-fire Holiday AF game, where Logan reveals her takes on real vs. fake trees, ATL vs. LA, sweet potato vs. peach cobbler, eggnog vs. champagne, tropical vs. snowy Christmases, and board games vs. caroling — including her hilarious disdain for cooked fruit and her competitive streak that once left 17,000 PIT opponents defeated.

Filled with warmth, laughter, reflection, and holiday chaos, this episode shines a light on Logan’s heart, humor, and cultural roots.

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Comedian, entrepreneur, and cultural favorite KevOnStage sits down with hosts Deborah Joy Winans Williams and MAJOR. for a wildly funny and surprisingly heartfelt holiday conversation on Choosing Joy for the Holidays. From broke-era Christmases to the infamous Batman-without-the-Batman gift, Kev shares stories that shaped his childhood — and why those moments still make him laugh today.

Kev opens up about what the holidays were like growing up with very little, including years when presents were missing, sweaters were the wrong size, and his grandmother still made it all feel meaningful. He reflects on how becoming a father shifted everything, including why he eventually stopped giving his kids mountains of gifts and instead started taking annual Christmas trips around the world — this year, all the way to Japan.

As a comedian who happens to be a Christian (and not the other way around), Kev breaks down how he navigates faith, comedy, and community without letting labels box him in. He shares outrageous stories about church life, roasting from the pews, and learning not to fear disappointing people — because, as he says, “I disappoint myself every day.”

The episode closes with a rapid-fire holiday game featuring eggnog, NBA basketball vs. Christmas service, the best version of “This Christmas,” and which family member is absolutely spiking the eggnog.

A hysterical, warm, relatable, culturally rich episode — everything Holiday AF was built for.

Podcast: https://podcasts.apple.com/us/podcast/choosing-joy/id1826833726

Instagram: https://www.instagram.com/thechoosingjoypodcast/

TikTok: https://www.tiktok.com/@choosingjoythepodcast

See omnystudio.com/listener for privacy information.

Actress, comedian, and all-around powerhouse Bresha Webb joins Holiday AF for a wildly entertaining and heartwarming conversation about family traditions, Christmas nostalgia, and the joy of giving. Hosts Deborah Joy Winans Williams and MAJOR. dive into Bresha’s childhood holiday memories growing up in the Webb household, including her father’s annual Christmas breakfast ritual and her mother’s legendary home-cooked apples. Bresha shares how the holidays have evolved as her parents get older — and how she now flies them to Los Angeles to keep their family traditions alive.

She also opens up about working with Tyler Perry on A Fall From Grace, stepping into a dramatic role alongside legends like Cicely Tyson and Phylicia Rashad, and what it meant to portray a character audiences hadn’t seen from her before.

Of course, it wouldn’t be Holiday AF without games — Bresha brings her iconic impressions to holiday classics, performing Silent Night as DMX, Britney Spears, and the incomparable Beverly Uggams. From laughter to love to full-on festive chaos, this episode captures the spirit of the season in the most joyful way.

If you love Bresha Webb, comedy, Christmas traditions, or holiday nostalgia, this episode brings all the festive magic.

Podcast: https://podcasts.apple.com/us/podcast/choosing-joy/id1826833726

Instagram: https://www.instagram.com/thechoosingjoypodcast/

TikTok: https://www.tiktok.com/@choosingjoythepodcast

See omnystudio.com/listener for privacy information.

Actor Ser’Darius Blain, known for his breakout role in the Jumanji franchise, joins Holiday AF for a warm, funny, and inspiring conversation with hosts Deborah Joy Winans Williams and MAJOR.. Born in Miami to a Haitian and Dominican family and raised with a blend of Southern and Caribbean traditions, Ser’Darius reflects on how his multicultural upbringing shaped the way he celebrates the holidays.

He shares how he secretly nurtured a passion for acting while following a pre-med track, eventually dropping out of medical school to pursue his dream in New York — where he also experienced his very first “white Christmas.” Ser’Darius dives into the foods that defined his childhood holidays, including cornbread, collard greens, curry goat, oxtail, griot, rice and peas, and Haitian-style legume.

As he reflects on family traditions, Ser’Darius talks about the improvisational nature of Caribbean-American Christmases, the last-minute planning, and the joy that always comes from bringing everyone together. Now in adulthood, he’s created a new tradition: flying his family to a different holiday destination each year, from New York to Big Bear, as a way to give them the gift of exposure and togetherness.

He shares stories from booking Jumanji, his shock at being cast as a high schooler at 30, and the lessons he learned watching superstars work up close. The episode wraps with a fun conversation about his culinary skills and his holiday cooking company, King’s Cuisine.

This episode blends culture, comedy, warmth, and legacy — everything that makes the holidays meaningful.

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Actor, writer, and director Will Catlett joins Holiday AF for a soulful, funny, and uplifting conversation with hosts Deborah Joy Winans Williams and MAJOR.. Growing up in Del Ray, a small neighborhood in Alexandria, Virginia, Will reflects on the meaning of a true winter holiday — the cold air, the change of seasons, and the traditions that shaped his childhood. Now raising a daughter of his own, Will shares how fatherhood has transformed him as an artist and why seeing his heart “outside of himself” brings new meaning to the Christmas season.

Will opens up about the holiday rituals he wants to pass on, including his mother’s beautifully decorated Christmas trees, the Black snowman that sat in their window, and the excitement of embracing both joy and cultural representation in his home. He also talks about discovering acting in college — a chance encounter at Foot Locker that led to an acting class and changed the course of his life forever.

The episode takes a hilarious turn as Will participates in the Holiday AF acting game, improvising as an overworked elf named Heathcliff, and later stepping into the role of Santa Claus during a playful skit with Mrs. Claus. The conversation ends with moving reflections on purpose, legacy, and using art as a way to affect change.

This episode blends humor, heart, culture, and craft — a meaningful holiday listen for fans of Will Catlett’s work and spirit.

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Actress, writer, and rising NBC star Michele Weaver joins hosts Deborah Joy Winans Williams and MAJOR. for a warm, funny, and joy-filled conversation on Holiday AF. Known for her breakout roles in Love Is___ and her upcoming NBC family drama, Michele shines as she shares the unexpected path that shaped her career — from graduating without an agent to working as a makeup model, phone rep, and airbrush artist before landing her first roles.

Michele reflects on her creative journey, including directing The Glass Menagerie as a high school senior and later working behind the camera with Deborah on a short film. She opens up about her growing passion for storytelling, the excitement of starring in a new NBC series, and the joy of stepping into a character who feels like family.

The holiday conversation takes center stage as Michele reveals her lifelong obsession with eggnog — yes, even the dairy-free kind — and breaks down her family’s Secret-Santa-style name-draw tradition. She talks about growing up in snowy Denver, why she’s never had a Los Angeles Christmas, and the spiritual comfort she found as a child praying for snow so she’d “know everything was okay.”

This episode blends laughter, nostalgia, friendship, and holiday magic — a beautiful showcase of Michele’s heart and humor.

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Actress, comedian, and all-around powerhouse Bresha Webb joins Holiday AF for a wildly entertaining and heartwarming conversation about family traditions, Christmas nostalgia, and the joy of giving. Hosts Deborah Joy Winans Williams and MAJOR. dive into Bresha’s childhood holiday memories growing up in the Webb household, including her father’s annual Christmas breakfast ritual and her mother’s legendary home-cooked apples. Bresha shares how the holidays have evolved as her parents get older — and how she now flies them to Los Angeles to keep their family traditions alive.

She also opens up about working with Tyler Perry on A Fall From Grace, stepping into a dramatic role alongside legends like Cicely Tyson and Phylicia Rashad, and what it meant to portray a character audiences hadn’t seen from her before.

Of course, it wouldn’t be Holiday AF without games — Bresha brings her iconic impressions to holiday classics, performing Silent Night as DMX, Britney Spears, and the incomparable Beverly Uggams. From laughter to love to full-on festive chaos, this episode captures the spirit of the season in the most joyful way.

If you love Bresha Webb, comedy, Christmas traditions, or holiday nostalgia, this episode brings all the festive magic.

Podcast: https://podcasts.apple.com/us/podcast/choosing-joy/id1826833726

Instagram: https://www.instagram.com/thechoosingjoypodcast/

TikTok: https://www.tiktok.com/@choosingjoythepodcast

See omnystudio.com/listener for privacy information.

Comedian, entrepreneur, and cultural favorite KevOnStage sits down with hosts Deborah Joy Winans Williams and MAJOR. for a wildly funny and surprisingly heartfelt holiday conversation on Holiday AF. From broke-era Christmases to the infamous Batman-without-the-Batman gift, Kev shares stories that shaped his childhood — and why those moments still make him laugh today.

Kev opens up about what the holidays were like growing up with very little, including years when presents were missing, sweaters were the wrong size, and his grandmother still made it all feel meaningful. He reflects on how becoming a father shifted everything, including why he eventually stopped giving his kids mountains of gifts and instead started taking annual Christmas trips around the world — this year, all the way to Japan.

As a comedian who happens to be a Christian (and not the other way around), Kev breaks down how he navigates faith, comedy, and community without letting labels box him in. He shares outrageous stories about church life, roasting from the pews, and learning not to fear disappointing people — because, as he says, “I disappoint myself every day.”

The episode closes with a rapid-fire holiday game featuring eggnog, NBA basketball vs. Christmas service, the best version of “This Christmas,” and which family member is absolutely spiking the eggnog.

A hysterical, warm, relatable, culturally rich episode — everything Holiday AF was built for.

Podcast: https://podcasts.apple.com/us/podcast/choosing-joy/id1826833726

Instagram: https://www.instagram.com/thechoosingjoypodcast/

TikTok: https://www.tiktok.com/@choosingjoythepodcast

See omnystudio.com/listener for privacy information.

Actor Tye White, known for his role as Kevin Satterlee on Greenleaf and his recent work on Chicago Fire, joins Holiday AF for a funny, heartfelt, and nostalgia-filled conversation with hosts Deborah Joy Winans Williams and MAJOR.. As he approaches his second Christmas as a husband, Tye opens up about what the holidays look like in marriage — and how they’ve shifted since tying the knot.

Tye shares how spending Christmas in Los Angeles didn’t feel quite right, and why his wife’s British roots have now brought them to celebrating in London, where he’s adjusting to roast dinners, Yorkshire pudding, cauliflower mash, and the shocking absence of mac and cheese, collard greens, and sweet potatoes. He reflects on how their families have blended, the cultural differences that cracked him up, and the joy that comes from gaining a second family overseas.

A lifelong Christmas lover, Tye describes how the holiday season starts for him right after Halloween — complete with Temptations Christmas on repeat and drinks flowing from morning mimosas to evening eggnog. The conversation turns playful as he and Deborah revisit their Greenleaf chemistry, step into a “Newlywed Game” inspired challenge as their characters, and debate who was truly the worst parent on TV.

This episode is packed with humor, heart, culture, and Christmas chaos — a perfect listen for fans of Tye White and festive storytelling.

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