Watch: Footage shows Pezzola breaching Capitol on 6 January
Dominic Pezzola, 46, who was convicted of assaulting police and obstructing an official proceeding, was sentenced to 10 years in prison.
Ethan Nordean, 32, who led the group's march on Congress on 6 January 2021, was sentenced to 18 years for a more serious seditious conspiracy charge.
The former head of the group, Enrique Tarrio, will be sentenced next week.
Before being sentenced, Nordean told the court: "I would like to apologise for my lack of leadership that day" and called the riot "a complete and utter tragedy".
"To anyone who I directly or even indirectly wronged, I'm sorry," he said.
But US District Judge Timothy Kelly told him that the events of the day broke a long political tradition.
"If we don't have a peaceful transfer of power in this country, we don't have anything," Mr Kelly said.
Nordean, of Washington state, went by the nickname "Rufio Panman" and was well-known within the Proud Boys for his frequent brawls with antifa activists in the Pacific Northwest.
His sentence is one of the longest ones yet handed to Capitol riot defendants. Stewart Rhodes, the leader of the Oath Keepers militia, was also given 18 years in prison earlier this year.
The other defendant sentenced on Friday, Pezzola, a 46-year-old former US Marine, fought with officers during the riot and smashed a window with a police riot shield.
A selfie video taken on the day of the riot shows Pezzola smoking what he described as a "victory cigar" in the Capitol building.
While he was convicted on the assault and obstruction charges, he was acquitted of seditious conspiracy - a charge applied to defendants for plotting to overthrow the government or use force "to prevent, hinder, or delay the execution of any law of the United States".
An emotional Pezzola expressed some remorse for his actions during his sentencing hearing. His wife, daughter and mother all addressed the judge, with his mother describing him as having been a "wonderful child" that "never gave me any trouble".
Pezzola's wife said that her daughters have become victims of harassment and bullying at school.
But once the prison term had been handed down and the judge had left the room, Pezzola raised a fist and shouted: "Trump won!"
The Proud Boys - which started as an all-male, hard-drinking, self-described "Western chauvinist" fraternity seven years ago - saw themselves as Donald Trump's foot-soldiers and were among the first to march on the Capitol on the day of the riot.