Cabana Boys Events

Think you've got the charm of a leading man and the swagger of a cowboy? We're looking for you. The Broadway Boyfriends Bar Crawl is a one-of-a-kind nightlife experience, and the Cocktail Cowboy is the heart of it. You'll lead a crowd of excited guests through a multi-stop bar crawl — fully in character, fully costumed, and fully committed to giving everyone the night of their life. This isn't a side gig. It's a performance. What you'll be doing: Leading groups between venues as their charismatic cowboy guide Keeping the energy high and the crowd engaged at every stop Reading the room and bringing your best improv instincts to every moment Embodying the Broadway Boyfriend brand — think rugged, romantic, and ridiculously fun You're a great fit if you: Have a background in acting, musical theatre, or live performance Love working a crowd and naturally draw people in Can sustain character and high energy for a full event Are reliable, professional, and take the craft seriously Compensation: Flat day rate + tips + commission Commitment: Recurring events — join our roster and work regularly