Warning: SPOILERS ahead for The Politician season 1.
Netflix series The Politician was created by the makers of Glee and stars Ben Platt, a Broadway actor and singer-songwriter who is known for his role in the Pitch Perfect movies - so it's no surprise that the show has some singing in it. Protagonist Payton Hobart's main goal is to become student body president and, one day, President of the United States, but he's also a talented pianist and singer who gets to show off his vocal chords several times over the course of season 1.
The first song performed by Platt is in The Politician's pilot. After Payton's former paramour and opponent in the election, River Barkley, shockingly commits suicide in front of him, Payton sings Joni Mitchell's "River" at the school's memorial service, eliciting tears from many in the crowd. Originally released on Mitchell's iconic 1971 album Blue, "River" has since been covered by many other artists, including James Taylor, Sarah McLachlan, and Barry Manilow.
Later in the series (and possibly just as an excuse to have the character sing again), Payton decides to enjoy his final year of high school by taking part in a musical: Stephen Sondheim's Assassins. Set in a fantastical carnival shooting range, the musical explores the motivations of different assassins who have either killed, or attempted to kill, U.S. presidents. In Saint Sebastian High School's version, Payton plays John Hinckley, Jr., who tried to kill Ronald Reagan, and Infinity plays Lynette "Squeaky" Fromme, one of two women who attempted to assassinate Gerald Ford.
As Hinckley and Fromme, Payton and Infinity sing a duet called "Unworthy Of Your Love." The "Jodie" that Payton is singing to in this song is actually Jodie Foster, since Hinckley was obsessed with the actress, and the "Charlie" that Infinity sings to is Charles Manson, as Fromme was a devoted member of the Manson family. Appropriately, they sing this song in an episode titled, "The Assassination of Payton Hobart," in which Payton undergoes not one but two assassination attempts in his new role as student body president.
In the season finale, "Vienna," Payton is living in New York and working as a piano player and singer in a local bar. At the start of the episode he sings a song by Billy Joel called "Vienna" (hence the episode title). The lyrics of the song address a young person who, like Payton, is full of ambition and trying to race to their finish line. "Vienna" offers the advice to "cool it off before you burn it out," and to "take the phone off the hook and disappear for awhile" - which is more or less exactly what Payton is forced to do after his career as student body president ends in disaster and disgrace. Hopefully he'll be able to heed Billy's advice in The Politician season 2, or his next campaign could end as badly as the last.