Early career in Iowa Reeves began to get into musical recording at the end of high school, with his first CD being a self-produced album with a run of about 200 copies. After graduating high school, he went on to attend college at the nearby
University of Iowa but quickly dropped out due to a lack of interest. He continued on with music, playing at local venues and bars. Blue offered to have Reeves come out to his California studio, Revolver, to record some tracks together. Reeves accepted and flew out to Los Angeles, California, with the intention of recording and coming back to Iowa.
Mikal Blue and Colbie Caillat Reeves arrived in California around February 2005 and met with Blue to begin recording songs. Shortly after arriving, Blue introduced Reeves to a young female singer he was working with,
Colbie Caillat. Caillat and Reeves formed a quick friendship and Caillat's family invited Reeves to stay with them during his recordings with Blue. This eventually became Reeve's home as he decided to stay in California and not return to Iowa. The popularity of the Myspace-hosted song "Bubbly" led to a record deal for Caillat with
Universal Republic Records. The song "
Realize", which featured vocals by Reeves, also performed well on the charts. Reeves and Caillat won three
ASCAP awards for these two songs. Reeves continued to work on his own music as well, and in 2007 self-released the album
The Magnificent Adventures of Heartache (And Other Frightening Tales...), which was likewise produced by Mikal Blue, as well two tracks produced by Stuart Brawley. The album had modest success on
iTunes, debuting at No. 2 on the folk charts and went to being named one of the top indie albums of the year on iTunes. DioGuardi and Reeves would end up working together on music, most notably co-writing the song "Terrified" which they would perform together on YouTube and
Lopez Tonight. Songs from that and previous albums would also be featured on TV shows such as
Army Wives and
One Tree Hill around this time. but the album was put on hold during the transition at Warner. Bros Records when CEO Tom Whalley stepped down in September 2010. The album featured collaborations with Kara DiaGuardi and Colbie Caillat. Warner Bros. Records eventually released a track from the album, "Helium Hearts", as a single in July 2010. With the single, a
music video was also released. Months passed and Reeves was dropped from Warner Bros. Records following the aftermath of Tom Whalley leaving, but was allowed to keep his master tapes. He self-released the album
The Lovesick in August 2011, a whole year after the initial single was released and nearly four years since his last full-length album. On November 15, 2011, Reeves released another EP,
Caged Birds Set Free, which hailed back to acoustic styles from
The Magnificent Adventures of Heartache. The EP features a re-recording of "Wishing Weed" featuring Colbie Caillat and a song featuring Kara DioGuardi, "New York in Wintertime". Reeves also continues to work as a co-writer, writing songs for such artists as
Lenka,
Angel Taylor,
Demi Lovato,
The JaneDear Girls and the Japanese group Kimaguren. The song "
The Show" that Reeves co-wrote with artist Lenka did well, being used in advertisements for
Old Navy and
Ugly Betty. "The Show" was also featured in the films
Moneyball and
Angus, Thongs and Perfect Snogging.
Songs Are Silent Films Reeves released his new full-length album called
Songs Are Silent Films on June 12, later than expected, on all digital retailers. He again worked with Nashville Producer, Adam Smith, on many of the tracks. Through pledgemusic.com, Jason asked fans to pledge to support the production of his new album, after being dropped by the Major Label. Pledgers get access to updates about the album as well as some of the songs to be released on the album. “There's a little bit of everything on it," Reeves said about the new record. "It goes from really stripped-down acoustic to full band. There's a couple things on there that I’ve never tried before, but for the most part it's a return to the way I have been doing it all along – just the acoustic, organic feel." The first song from the album is called "Back With Me" and was released on March 27 along with a video on YouTube, which was directed by Reeves. The second promotional released song from
Songs Are Silent Films is "You're My Best Friend" and was released on April 17. The first official single is called "More In Love With You" and features
Nelly Joy, who formerly recorded under her real name Danelle Leverett as one-half of
the JaneDear girls.
High Dive Heart Reeves released the single "Vintage" on April 21, 2015, from his newest project
High Dive Heart, a pop duo consisting of himself and
Nelly Joy, who formerly recorded under her real name Danelle Leverett in the group
the JaneDear girls. On July 17, 2015, High Dive Heart released their first EP:
Sonic Graffiti – EP. ==Personal life==