After a two-year hiatus, Timberline Learning Center’s Wit and Wine is returning to raise funds for the preschool. Its biggest fundraiser of the year features comedy from Danny Jolles and Derrick Stroup, a silent auction, beer and wine.

Leslie Davis, executive director of Timberline Learning Center, said event started small at the Motherloaded Tavern before getting bigger and moving to the Riverwalk Center. However, as the economy worsened and less live events happened, Davis said it moved to the Speakeasy Theater — what is now The Eclipse Theater — for about six years.

Now Davis is excited for the 10^th annual event to return to the Riverwalk. Davis said it is geared less toward parents of students and more for anyone in the region, especially fans of stand-up comedy.

“Have some laughs, let your hair down and see all those faces from the community that you haven’t seen because everyone is slowly rebuilding their lives,” Davis said.

The evening historically raises between $15,000 to $20,000 in net profits that go directly back to the school. This year, the money will be used for enhancements for playgrounds and outdoor learning spaces, such as steps, rocks and other climbing surfaces. Davis said respect and appreciation for the natural world is a key tenant of the school.

“If we’re able to focus on these renovations and upgrades, it will provide environments for students to think critically, work collaboratively and independently and connect with nature in an authentic manner,” Davis said.

Presented by BGV Gives, the evening’s wine comes from Blue River Bistro while the beer is from Basecamp Wine and Liquors. A few of the silent auction items are jewelry, skis, rounds of golf, Patagonia jackets and an e-bike. They’ve also assembled gift cards from all over to create packages like pizza or date nights for a year.

Stroup will be opening for the event. Originally from Jacksonville, Alabama, he started his comedy career in the South but has been living in Denver since 2015. Accolades include being a finalist at Comedy Works’ New Faces Competition and opening for comedians like Frank Caliendo, Brian Posehn and Josh Blue.

Stroup also shot a Dry Bar Comedy special that will be released this year.

Headlining is Los Angeles-based Jolles. Best known for playing George in Rachel Bloom’s CW series “Crazy Ex-Girlfriend,” Jolles grew up in Virginia before studying theater at New York University. He eventually moved to stand-up comedy because, in his mind, it felt like everybody got an equal shot versus acting. He’s been doing it for 12 years and counting. Jolles earned a New Faces spot at the Just for Laughs Festival in 2017, and he is also an original member of the sketch comedy group Sasquatch alongside Jack Quaid, Nick Williams and Zach Webber.

“It all started from loving the art form and wanting to be part of it, starting terrible and getting better every day,” Jolles said.

However, acting and comedy aren’t mutually exclusive for Jolles. He can act in commercials and shows like “Ramy” and “Corporate” in the day then crack jokes for audiences at night. He recently performed in the horror film “V/H/S/99” and can be seen in Damien Chazelle’s upcoming period piece “Babylon.”

“I never felt I had to choose,” Jolles said. “I love both with all my heart, and I hope to do both for the rest of my life.”

But if he had it his way, Jolles said he would be doing every musical theater TV show out there to continue to sing like he did on the critically acclaimed “Crazy Ex-Girlfriend.” 

“The fact that I got to be in a show that was run by a friend — so I was able to feel comfortable growing — was incredible to me,” Jolles said.

Jolles takes pride in his unique approaches to comedy. Last year, he released a special that was filmed in six different locations. In October he came out with “You Choose,” an interactive choose-you-own-adventure special. It took Jolles over a year to write it and he worked on it in between outdoor performances and other pandemic projects.

“It’s unlike any special you’ve ever watched before,” Jolles said. “You get to choose my jokes and literally have a special just for you.”

The first questions asks if one cares about Jolles getting engaged and then leads to a different clip depending on what is clicked. The pro or con dynamic continues as segments ask for opinions on David Blaine or conspiracies, and then the next bit is based on that reaction.

Jolles jokes about seven different topics, creating a multitude of different paths for viewers that leads to a finale on truth and persuasion.

While that special is made for YouTube, Jolles said audiences will have unique time in Breckenridge, too. He argues that comedy stands apart from live concerts or live theater since those follow set lists or scripts even though he may tell the same jokes. 

“Every show live in stand-up comedy is personal to that moment, and that is what I’m most excited about,” Jolles said. “… I plan to make that show as special as anything.”