Prior to launching his musical career, Grand modeled under a number of pseudonyms; he was a cover model for Australia’s DNA magazine in 2011 with a photo session shot by photographer Tom Cullis. He played piano at four Chicago-area churches and at various clubs in Chicago, most notably The Joynt in downtown Chicago, until 2013. He also performed cover songs, including hits by Lady Gaga, Bruno Mars, One Direction and Journey, and uploaded these to YouTube under the name Steve [Starchild]. However, Grand wanted to release original music.

On July 2, 2013, Grand uploaded a music video for his song “All-American Boy” to YouTube—producing it himself at a cost of US$7,000. The video almost immediately went viral. Just eight days later, “All-American Boy” had more than 1 million views. The song, set against a backdrop of country roads, an American flag and friends around a campfire, tells the story of a young man in love with a heterosexual male friend. Grand recorded the vocals in his parents’ basement and maxed out his credit card to self-fund the video. The video was directed and edited by filmmaker Jason Knade. Buzzfeed ranked the video for “All-American Boy” on its list of the “24 Most Brilliant Music Videos from 2013”, and Out magazine named Grand to its annual “Out100” list of the year’s most compelling LGBT people. On July 18, 2013, Grand made his television debut, performing “All-American Boy” on WLS-TV produced program Windy City Live.

On September 6, 2013, Grand released “Stay”, the follow-up single to “All-American Boy”. followed by “Time” in 2014.

Steve Grand has become a media-sought figure as a gay young artist. In 2013, he appeared on Out magazine’s “Out100” list of prominent LGBT people. He also appeared in 2013 on Instinct gay American magazine’s cover as one of its “Leading Men”.

On June 20, 2014, Grand performed at the WorldPride Toronto 2014 opening ceremonies. Steve Grand performed during the ceremony along with Melissa Etheridge, Deborah Cox, and Tom Robinson. Toronto, with a population of approximately 6.4 million people, held 3 marches over 3 days: Trans march, Dyke march, and the WorldPride Parade.

In 2014, he was one of the performers at the opening ceremonies of WorldPride in Toronto, Ontario, Canada.

He announced plans to release his debut album financed by a successful Kickstarter public funding campaign. Just one day after the launch, the original $81,000 goal had been reached and in within 5 days, double the original funding goal, and by close, $326,593 had been pledged by 4,905 backers. The album titled All-American Boy was released on March 24, 2015. Since releasing his first album, Grand has travelled across the United States performing at Gay Pride Festivals and supporting gay causes.

In June 2015, Grand made his first trip to Europe as an Arts Envoy of the Bureau of Educational and Cultural Affairs for the U.S. State Department. He and his band promoted LGBT rights in Austria. While in Austria, he gave a talk and did a video for the local NGO “It Gets Better.” He gave a concert hosted by the Tri-Mission Ambassadors at the residence of Ambassador Alexa Wesner, a concert for Vienna’s LGBT community as well as a concert at the Pride festival in Graz. He also performed at Europride in Riga, Latvia.

In December 2015, Grand produced a bluesy and soulful reprise of Mariah Carey’s “All I Want for Christmas Is You”.

In June 2015, Steve was interviewed by Johnny McGovern and described his coming out process as well as his musical development through his first album.

In December 2015, Steve went public with his move toward sobriety.

In June 2015, Steve Grand visited Riga, Latvia, to teach a master’s class and to take part in the Europride festival that was held in the country’s capital city.

In March 2016, Grand and singer/songwriter Eli Lieb co-wrote a duet “Look Away” (This music video is unrelated to the song with the same name by Chicago.) By November 2016 the music video had received over 1,000,000 views on YouTube.

In 2016, Grand was included in Out Magazine’s 100 Most Eligible Bachelors. In May 2017 Steve was named the #3 most eligible Gay Bachelor by Attitude Magazine.

In March 2017, Grand performed at the Gay Mardi Gras in Sydney, Australia and Gay Pride Tampa, Florida.

Grand made his acting debut in December 2017 on the web series “Falling for Angels” (a Here TV/Pride Media project).

Grand’s second album, “Not the End of Me,” was released on July 6, 2018. The music on this album reflects Grand’s development as an artist and performer with a wide array of songs capturing his moods and personal experience. Not The End Of Me appeared at number 10 on the Billboard independent charts for the week of July 21, 2018.