Chamling was elected as the president of Yangang Gram Panchayat in 1982. In 1985, he was elected to the Sikkim Legislative Assembly for the first time. After being elected for the second time from Damthang constituency, he became the Minister for Industries, Information and Public Relations from 1989 to 1992 in the Nar Bahadur Bhandari cabinet.
His party first came to power in Sikkim after winning the 1994 assembly elections.
His popularity kept soaring in Sikkim due to his developmental work and for maintaining peace. He became the chief minister fifth time, a record previously hold by Jyoti Basu who ruled West Bengal from 1977 to 2000.
After 18 months of 2014 elections id est (that is) on November 30, 2015, 7 out of 10 opposition MLAs joined the SDF party under the leadership of Pawan Chamling. Now the ruling front has 28 out of 32 assembly seats in the state.
28 SDF MLAs 3 SKM MLAs 1 Independent Modern Language Association
On 18 January 2016 Prime Minister Narendra Modi made a two-day visit to the state to declare Sikkim as the first and the only Organic State in the country.
After a series of major political upheavals in Sikkim, Chamling formed the Sikkim Democratic Front on 4 March 1993. Chamling is the only chief minister of India who has governed a state five terms in a row, with his party Sikkim Democratic Front winning the 1994, 1999, 2004, 2009 and 2014 Sikkim legislative assembly elections.