Bug
Location: Steppenwolf Theatre
Date: January 23 – March 8, 2020

Among filmgoers, Tracy Letts is probably most recognizable as the dad in “Lady Bird,” but he has had a long and fruitful career as a playwright, including a Pulitzer win for his 2007 play “August: Osage County.” One of his earliest works was 1996’s “Bug,” about a lonely waitress living in a motel who falls for a conspiracy theorist and slowly loses her grasp on reality. The show is making its Chicago debut at Steppenwolf Theatre, where Letts has debuted many of his plays, and will star Letts’ wife Carrie Coon, most famous for her role in the critically acclaimed TV show “The Leftovers.”

King Princess
Location: Riviera Theatre
Date: February 5, 2020

In the span of two years, 21-year old artist King Princess has quickly established herself as a talented artist with a devoted fanbase. After her 2018 debut single “1950” received 300 million plays on Spotify and praise from big celebrities like Harry Styles, King Princess (the stage name of Mikaela Mullaney Straus) released her debut EP “Make My Bed,” followed by her first album “Cheap Queen” in 2019. The genderqueer openly gay artist is having a big year in 2020, opening for Styles’ tour in the summer, but before that she’ll be coming to Chicago during her Cheap Queen Tour.

Trixie Mattel
Location: Park West
Date: February 19, 2020

One of the most successful alumni from RuPaul’s Drag Race, Trixie Mattel finished sixth on the seventh season of the reality show, only to come back and triumph during the third season of All-Stars. Since then, she’s released two albums, started her own cosmetics brand, and released a comedy special. Now she’s going on tour, in a comedy/music revue backed with a live band.

Hayley Kiyoko
Location: Byline Bank Aragon Ballroom
Date: February 28, 2020

In the pantheon of Disney Channel actors turned pop stars, Hayley Kiyoko of Lemonade Mouth fame flies slightly under the radar, but the passion of her fanbase rivals her more mainstream counterparts. Dubbed Lesbian Jesus, Kiyoko’s music speaks frankly about her sexuality and her relationships with women, and has led to her developing a massive following in the queer community (back in 2018 she managed to singlehandedly make #20GAYTEEN trend which was quite frankly iconic). Kiyoko released an EP, “I’m Too Sensitive For This Shit,” and will be promoting the songs with a tour this Winter.

Duro Olowu: Seeing Chicago
Location: Museum of Contemporary Art
Date: February 29-May 10, 2020

Duro Olowu is a Nigerian-born fashion designer based in the United Kingdom who has designed for clients like Michelle Obama and Solange Knowles. His work is inspired by his Nigerian background, and is characterized by vibrant colors and sharp patterns. The Museum of Contemporary Art is hosting an exhibition curated by him, featuring some of his own work mixed with art from Chicago’s public and private art collections that suits his unique design sensibility.

What the Constitution Means to Me
Location: Broadway Playhouse
Date: March 4-April 12, 2020

A finalist for the 2018 Pulitzer Prize for Drama, “What the Constitution Means to Me” is a partly autobiographical work from Heidi Schreck, who wrote and stars in the play. As a teenager, Schreck competed in debate tournaments about the Constitution as a way to raise money for college, and “What the Constitution Means to Me” explores her struggle with how she views the document. Touching on feminism, abortion and immigration, and concluding with a live debate on whether or not the Constitution should be abolished, this is one of the most timely and relevant plays to hit Broadway in years.

My Dad Wrote A Porno Live Show
Location: Chicago Theatre
Date: March 7, 2020

With over 200 million downloads and counting, “My Dad Wrote A Porno” is one of the most popular comedy podcasts around. The show is hosted by Jamie Morton, James Cooper and Alice Levine as they dive into the world of “Belinda Blinked,” Morton’s dad’s erotic novel series following salesgirl Belinda Blumenthal’s sexual escapades in the wild world of the pots and pans industry. The three hosts are coming to Chicago March 7 for their live show tour, where they’ll read a chapter from the upcoming installment in the series where Belinda turns 30.

Billie Eilish
Location: United Center
Date: March 24, 2020

In 2019, the pop music industry was defined by fresh new talent dominating the charts, from Lil Nas X to Lizzo. One of the biggest and best of this new wave of artists is 18-year old Billie Eilish, who previously came close to her breakout in 2017 when her debut EP “Don’t Smile at Me” reached number 14 on the Billboard album chart. 2019 saw her release her first full-length album, “When We Fall Asleep, Where Do We Go?,” which hit number one, received critical acclaim and spawned six top 40 singles, including the number one song “bad guy.” Eilish is a distinctive artist notable for her goth-inspired style and image, ethereal husky voice and visually dynamic live performances. She’s currently on a tour to promote “When We Fall Asleep, Where Do We Go?,” which hits Chicago March 24.

Frida Kahlo, Her Photos
Location: National Museum of Mexican Art
Date: April 3-August 2, 2020

One of the best and most accessible museums in Chicago is the National Museum of Mexican Art. Located in the Pilsen neighborhood, the museum is completely free, and features a wide variety of artwork from Mexico and Mexican communities in the U.S. This winter, they’re opening an exhibition of personal photographs from famed Mexican artist Frida Kahlo, which captures several of the subjects that would inspire her paintings, including her family, political protests, and indigenous communities.

Soccer Mommy
Location: Thalia Hall
Date: April 11, 2020

Indie rock artist Sophie Allison, better known by her stage name Soccer Mommy, has worked since 2015, releasing three albums between 2016 and 2018. It was the last of those releases, “Clean,” where she came into her own, delivering one of the best albums of that year, characterized by catchy hooks and raw, emotionally honest lyrics. Last year, she released two new singles, “yellow is the color of her eyes” and “lucy,” and will be going on tour this year. Opening for her is folk artist Tomberlin, who released her debut album “At Weddings” in 2018.

Nickelodeon’s JoJo Siwa D.R.E.A.M The Tour
Location: Allstate Area
Date: April 14, 2020

After getting her start on iconic reality series “Dance Moms,” Jojo Siwa has exploded as an icon for kids and kids at heart everywhere. With over 10 million subscribers on her Youtube channel where she posts daily vlogs, a contract with Nickelodeon and multiple appearances in the channel’s specials and 20 million Spotify streams on her bop of a single “Boomerang,” Siwa has established herself as a brand, and a powerful one at that. She is currently on tour to promote her EP “D.R.E.A.M.” See her at the Allstate area to catch a glimpse of her iconic high-ponytail, multi-colored bows and glitter tracksuits that can match any Met Gala look anyday.

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Twitter: @wilsonchapman6