Happy Pride Month, listeners! 🏳️🌈 To kick off the celebrations, the incredibly brilliant Canadian comedian, TV personality, and pop-culture maven Tranna Wintour is back on my podcast again! This week, we are taking a deep dive into the underrated/forgotten gems from the Queen of Pop. Madonna has given us decades of era-defining anthems, but what about the masterpieces that often get overlooked, even with some of her biggest hits? Tranna and I lay out my personal Top 10 underrated and forgotten Madonna hit songs, analyzing the impact, cultural legacy, and our personal connections to each track. Plus, we look ahead to July 3rd, breaking down everything we know so far about her highly anticipated fourteenth studio album, Confessions II, her first album since Madame X back in 2019. From the Stuart Price reunion to the electronic club beats, we are ready to get back to the dance floor. Inside the Episode: [00:00] Pride Month Kickoff & catching up with Tranna Wintour. [12:15] The Countdown: Tracks 10 through 6—The mid-90s gems and overlooked synth-pop. [35:40] The Top 5: The most criminally forgotten Madonna singles and their cultural impact. [52:10] Confessions II Preview: Analyzing the lead singles, samples, and what to expect on July 3rd. Bio: Tranna Wintour is a highly-acclaimed bilingual comedian, singer, writer, hostess, and producer. Legendary comedienne Sandra Bernhard described her as “a candle in the window on a cold, dark winter’s night.” A Just For Laughs New Face Canada (2019), Tranna was named one of the queens of Canadian comedy by Fashion magazine. Performing in both English and French, she appeared in a Juste Pour Rire gala in 2021 before starring in Québec’s hit series, Big Brother Célébrités. Her run to the top 4 was hailed as the show’s breakthrough moment and “the best moment on Québec TV in years” by the Journal Métro. Tranna co-hosted the successful CBC Podcast Chosen Family for three seasons, which was named one of Apple’s Best Podcasts for two consecutive years. Her debut album, Safe From Your Affection, is available on all streaming platforms, and she is currently developing an original comedy series with a major Canadian broadcaster. Also, check out her new podcast, The Blank List Substack: Tranna Wintour Instagram: TrannaWintour Website: https://www.trannawintour.com What’s your ultimate underrated Madonna track? Let us know in the comments below!