Straker independently released his album Songs from Highway 15 in 2006. The folk-pop album contains 10 songs inspired by people and places in Saskatchewan. It was recorded live with engineer Brian Moncarz in Toronto. Canadian singer-songwriter Kat Goldman sang backing vocals on the album. In 2008, Straker released his follow-up album Step Right Up, which included the songs "Hypnotized" and "Somewhere Between". A music video for "Hypnotized" was played on MuchMoreMusic across Canada. Step Right Up was re-released on MDM/Universal in 2010. The album was produced by Justin Gray in Toronto and Los Angeles. In 2011, Straker released the album under the soles of my shoes, produced by Dave Thomson in Nashville. The album was mixed by Grammy Award winning engineer Chad Carlson. Straker released a 9-song studio album, Vagabond, on 2 October 2012. The album was produced by Danny Michel. Piano tracks were recorded at the Canadian Broadcasting Centre in Toronto in studio 211, using Glenn Gould's Steinway & Sonsgrand piano. Fred Penner performed harmonica on the song "Birchbark Canoe". In 2014 the recording Live with CBC Radio was released. It was recorded by CBC Radio in the Mae Wilson Theatre in Moose Jaw, Saskatchewan. In 2015 Jeffery released North Star Falling produced by Dean Drouillard. The album debuted in the top 10 of the iTunes singer-songwriter charts in its first 2 weeks. On May 19, 2017, Straker released "Dirt Road Confessional", a 12 song recording with roots-folk influenced arrangements and instrumentation. The album was produced in 5 different studios by several producers: Daniel Ledwell ; Royal Wood and Lawrence Katz ; Dean Drouillard ; Brad Prosko and Murray Pulver ; Robyn Dell'Unto. The album contains 2 songs co-written with Royal Wood and Lawrence Katz, a single song co-written with Jay Semko, and one co-written with Karen Kosowski. Straker tours over 100 shows each year and performed his sold out orchestral debut with the Regina Symphony Orchestra in Regina Saskatchewan, October 2011. He has performed subsequent orchestral concerts of his work with the Saskatoon Symphony Orchestra in October 2013 and 2018 and the Sudbury Symphony Orchestra in 2015. Jeffery was the winner of the international category of the 55th Vina del Mar International Song Festival in February 2014 with his song Hypnotized. The singer-pianist is a regular national cast member of the long running telethon Telemiracle produced by the Kin Canada of Saskatchewan, Canada. The telethon is broadcast on CTV. He is represented by Paquin Artists Agency.
