Skehan was interested very early in music. In 2006, he became part of the global/international boy band project Streetwize (alongside Irish Lee Mulhern (later known as Lee Matthews), English Lee Hutton and Swedish Jonathan Fagerlund). The original members made a tour in Ireland, UK, Sweden, and appeared on the US television station CN8, a cable television station where they performed “Room in Your Heart” in a morning show hosted by Greg Coy. Skehan and Jonathan Fagerlund were disenchanted with the progress of the band and left early to be replaced by Venezuelan Antonio Jones and American Kyle Carpenter. Streetwize eventually folded without any hits.

An avid food enthusiast, Skehan started a blog in 2007 called Good Mood Food that evolved into a cookbook. After many appearances on television, and giving of live demonstrations at social events and shows, he was featured in his own weekly food programme, Kitchen Hero, on RTÉ One that was launched on 16 May 2011. In 2011, he published a cookbook based on the television series, Home Kitchen Hero – Bringing Cooking Back Home. A second series and a Christmas special were aired in 2012. UKTV network Good Food began airing the show in April 2012. The show is now in its sixth year of production.

On 23 February 2008, Skehan took part in Eurosong 2008 in a bid to represent Ireland in the 2008 Eurovision Song Contest with the song “Double Cross My Heart”. It was a pop song composed by Joel Humlen, Oscar Gorres and Charlie Mason, and performed by Skehan with two male and two female back-up dancers, as well as a male back-up singer. Skehan was one of the Final 6, alongside Dustin the Turkey, Maja, Leona Daly, Liam Geddes and Marc Roberts; with Dustin the Turkey winning with the song “Irelande Douze Pointe”.

In 2009, Skehan joined the Irish band Industry alongside the English Lee Hutton (his former bandmate in Streetwize) and Irish girl members Michele McGrath and Morgan Deane. Industry had success in the Irish charts including two chart-topping singles “My Baby’s Waiting” in June 2009 and “Burn” in August of the same year on the Irish Singles Chart. In 2009, they were also a supporting act for The Pussycat Dolls at Fitzgerald Stadium. Later Industry single releases like “In Your Arms”, “My Mistake”, “Drown in the Music” and “Kill the DJ” did not chart. The band broke up in 2010.

Skehan became a co-presenter and judge on Junior MasterChef on the BBC in 2012, appearing alongside John Torode. In 2013, after appearing on Jamie Oliver’s YouTube channel, Foodtube, Skehan launched his own dedicated YouTube channel which has since grown to over 800,000 subscribers.

In June 2015 he married Sofie Larsson in Dublin City Hall followed by a reception in Lisnavagh House in County Carlow and had their honeymoon in Ravello on Italy’s Amalfi Coast. In April 2016, Skehan and his wife moved to Los Angeles.

In June 2017, the couple announced that they were expecting their first child. In December 2017, their son was born in Los Angeles. In June 2019, the couple announced they are expecting a second child. At the end of November 2019, their second son was born.