He was a member of the Tjóðveldi until 26 May 2011, and left after disagreements with the leader of the party and the other members of the Løgting from Tjóðveldi regarding their work with preparing a bill for a Faroese constitution. Later that year, he joined Javnaðarflokkurin. Skaale was elected to the Løgting from 2008–2011, and was a member of the Committee on Cultural Affairs of the Løgting. He was also elected to the Danish Folketing 2007–2011, and covered for Høgni Hoydal from 19 February 2007 until 8 September 2008. The Faroe Islands has two members in the Danish Folketing. Skaale has been a member of the Folketing since 2011, and is the chairman of the Folketing's Faeroes group, part of Denmark's delegation to the Nordic Council and a member of the Folketing's foreign policy committee. Before the election to the Danish Folketing, Skaale and the Social Democratic Party promised the Faroese voters, that he and the other candidates of the party would not run for the Faroese Løgting as well, if they were elected, because they believed that it was impossible to be a full-time member of the Faroese parliament and a full-time member of the Danish Folketing at the same time. And Skaale kept his promise, he was not a candidate for the Faroese elections in 2011. At the 2015 Danish general election Skaale was a candidate for Javnaðarflokkurin again; he received 2495 personal votes and became the top scorer of all candidates of all parties in the Faroe Islands and was one of two candidates who got elected. Skaale was a candidate for the 2015 Faroese general election. He was not elected but ended as number 11 on his parties list, but because his party, Javnaðarflokkurin, formed government together with Tjóðveldi and Framsókn, four of the elected members of the Løgtings took leave because they were elected ministers, and Skaale could have taken seat in the Faroese parliament for Rigmor Dam who became Minister of Finance. Javnaðarflokkurin's policy now forbids their members to be a member of both parliaments at the same. Skaale can choose at some point to take leave from the Folketing in order to be a member of the Løgting, and during the electoral campaign he expressed that wish, because being full time and the whole time only in the Danish parliament distanced the Faroese members of the Folketing from what was going on in the Løgting.
His career as a comedian and singer
Skaale has had a number of acting roles, but is best known for the comedy seriesPipar & Salt, where he appeared with Jákup Veyhe, and for the lead in the comedy series E elski Førjar. E elski Førjar means "I love the Faroe Islands", but it is misspelled on purpose, the correct spelling would be "Eg elski Føroyar". In both comedy series, he sang several songs, of which some became quite popular. Some of the songs which he sings: From Pipar & Salt:
Eg havi tað strævið - as persona Esmar Eysturoy
Lívið er oyðilagt, tá gentur fáa makt, the song makes joke about a man who is afraid of female power. He sings this song while acting as the character Kári Cool in the Pipar & Salt series
Lat tey vita, ólavsøka er sings together with Jákup Veyhe and others. The song makes joke about the economical crisis in the 1990s which was especially hard on the island Suðuroy.
From E elski Førjar:
Danskt pjatt - from the series "E elski førjar" in the role as a Faroese man named Haraldur. The song makes joke about this Faroese man who lives in Copenhagen, he is married to a Danish women but despices everything which is typical Danish and loves everythings which is typical Faroese.