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In late 2015, Westerberg announced that he had formed a new band called The I Don't Cares with musician Juliana Hatfield. Their debut album, Wild Stab, was released in January 2016.

The Replacements began performing in the Twin Cities punk scene, showcasing Westerberg's songs in a classic rock–friendly punk style. The band made several albums for local label Twin/Tone before signing to Sire Records in 1985.

Upon Alex Chilton's death in March 2010, Westerberg wrote a eulogy for one of his biggest influences that appeared in The New York Times. In May 2010, he played "Dangerous Boys" and "Time Flies Tomorrow" standing on the visitors' dugout at Target Field for the documentary, 40 Nights of Rock & Roll. Westerberg appeared in the video for the title track of Glen Campbell's 2011 farewell to studio recording, a cover of Ghost on the Canvas (which Westerberg wrote in 2009). In the online, May 24, 2013, version of The New York Times' Measure for Measure feature, he set forth his songwriting creed, which privileges the virtues of inspiration and spontaneity over gradually developing and revising a song.

On July 21, 2008, Westerberg released an album with 49 minutes' worth of music for 49 cents. The album, 49:00... Of Your Time/Life, was taken down from Amazon.com and TuneCore store a few weeks later. In its place, Westerberg released a song titled "5:05" (in reference to the fact that 49:00 was really 43:55 long, 5:05 shorter than 49:00). From the lyrical content of "5:05," it is believed that 49:00 was recalled due to copyright issues in the ending cover medley.

On August 27, 2008, Westerberg released two new songs, "3oclockreep" and "Finally Here Once", on TuneCore. On September 13, 2008, another new song "Bored of Edukation" was released as an MP3 download on Amazon.com. On December 24, 2008, Westerberg released three songs; "Always in a Manger", the folk music standard "Streets of Laredo", and "D.G.T." on tunecore.com for $0.74. On September 22, 2009, Westerberg released an EP titled PW & The Ghost Gloves Cat Wing Joy Boys with six songs: "Ghost on the Canvas," "Drop Them Gloves," "Good as the Cat," "Love on the Wing", "Gimmie Little Joy" and "Dangerous Boys".

In 2006, Westerberg wrote a collection of songs for the animated film Open Season. In all, the soundtrack includes eight Westerberg originals. Two of the songs were covered by other artists. The track "Wild As I Wanna Be" is performed by Deathray, whereas Pete Yorn performs "I Belong (Reprise)." In addition, Tommy Stinson is featured playing bass on the songs "Love You in the Fall" and "Right to Arm Bears." The soundtrack also includes the song "Good Day" from Westerberg's solo album Eventually. The album is rounded out by two non-Westerberg originals, Deathray's own "I Wanna Lose Control (Uh Oh)" and the Talking Heads' 1986 hit "Wild Wild Life."

After he was seen on stage playing a First Act production model guitar, Westerberg collaborated with the Boston-based guitar manufacturer in September 2006 to create his signature edition PW580 with a red plaid pickguard.

In December 2005, Westerberg reconvened with Tommy Stinson and Chris Mars to record two new songs for a compilation titled Don't You Know Who I Think I Was?, which was released in 2006.

Westerberg quit the major label circuit for three years before staging a comeback in 2002. With new management and a new independent label, Vagrant Records, he released two records simultaneously, Stereo and Mono (Mono being released under his alter ego Grandpaboy). Stereo and Mono were recorded in Westerberg's basement studio. Westerberg became increasingly prolific, releasing Dead Man Shake (as Grandpaboy), Come Feel Me Tremble, and Folker all within the next two years.

Westerberg contributed a cover of The Beatles' "Nowhere Man" for the 2002 soundtrack to the 2001 film I Am Sam. Additionally, "Lookin' Up in Heaven" appears on the Starbucks sampler Hear Music, Vol. 10: Reveal, "Outta My System" can be found on Hot Stove, Cool Music, Vol. 1, and the Vagrant Records sampler Another Year on the Streets, Vol. 3 features "As Far As I Know." All three compilations were released in 2004.

In 1996, he released his second solo album, titled Eventually, which was tepidly received by critics and had modest sales. It did yield the alternative radio hit "Love Untold". Westerberg parted ways with Reprise Records and the following year chose to release songs that were more blues-influenced and less slickly produced under the name Grandpaboy. An EP and single were released by indie label Soundproof/Monolyth Records. His third album, Suicaine Gratifaction, is a piano-driven, melancholy, and highly personal work. The album was released on Capitol Records in 1999. The label was undergoing reorganization and the album was given minimal promotion. Westerberg appeared on a fifth-season episode of The Larry Sanders Show (entitled "Larry's New Love") performing "Ain't Got Me" from Eventually. The episode first aired on February 26, 1997. Westerberg also performed the song that same year on The Tonight Show hosted by Jay Leno.

Westerberg's first solo releases were two songs, "Waiting for Somebody" and "Dyslexic Heart", for the soundtrack to the 1992 Cameron Crowe film Singles, for which he is also credited with composing and performing the score. The following year, Reprise Records released his first solo album 14 Songs. During the interim between solo albums, Westerberg songs appeared on Melrose Place ("A Star Is Bored") and Friends (his cover of Jonathan Edwards' "Sunshine" and "Stain Yer Blood") television soundtracks, in 1994 and 1995 respectively. In 2007, "Dyslexic Heart" was used in Smart People movie trailer, a selection made by music supervisor Serena Undercofler.

Despite the jump to Sire, The Replacements never translated their critical success into commercial sales. The band broke up in 1991. Their final album, All Shook Down, was mainly a Westerberg solo project; there were a number of guest performers and the other three members of the band (including Slim Dunlap, who had replaced Bob Stinson three years earlier to tour in support of Pleased to Meet Me), made minimal contributions. Mars left the band soon after the album was released. After touring for the album (which was critically well-received) with replacement Replacements, Westerberg and bassist Tommy Stinson went their separate ways.

Westerberg co-wrote the song "Backlash" with Joan Jett for her 1991 album Notorious and played guitar with her on a video of the song. He also recorded a duet with Jett ("Let's Do It") for the Tank Girl soundtrack (1994).

Westerberg has had problems with alcoholism and kicked the habit solo in 1990. He has since resumed drinking occasionally in moderation.

In the late 1970s Westerberg was working as a janitor for U.S. Senator David Durenberger, and one day while walking home from work, he heard a band practicing Yes's "Roundabout" in a basement. He talked his way into the band by convincing the singer that the other band members — Bob Stinson, Chris Mars and Tommy Stinson — were going to fire him. The singer quit, and Westerberg joined the group. The band was originally called The Impediments, and they played their first gig in the basement of a church, playing to members of a nearby halfway house who did not appreciate their drunken shenanigans. They soon changed their name to The Replacements after several venues declined to advertise the band under their original name.

Paul Harold Westerberg (born December 31, 1959) is an American musician, best known as the lead singer, guitarist and songwriter in The Replacements, one of the seminal alternative rock bands of the 1980s. He launched a solo career after the dissolution of that band. In recent years, he has cultivated a more independent-minded approach, primarily recording his music at home in his basement.

Westerberg was born in Minneapolis, Minnesota, the son of Mary Louise (née Philipp) and Harold ('Hal') Robert Westerberg (1918–2003), an employee of Cadillac-General Motors. He has three sisters: Anne, Julie, and Mary. He married his first wife, Lori Bizer, in 1987. After their divorce, he married former Zuzu's Petals guitarist and author Laurie Lindeen. They divorced in 2014. They have a son, Johnny (born 1998), whose voice is likely on 49:00 and "Whatever Makes You Happy" from Westerberg's solo album Suicaine Gratifaction. Westerberg severely injured his fretting hand in 2006 in an accident while trying to remove candle wax with a screwdriver, leaving his ring finger on his left hand numb. The Replacements reunited in 2012, notably playing several dates at Riot Fest in 2013 and the Coachella Music Festival in 2014. The Replacements once again disbanded in 2015. He resides in Edina, Minnesota, a suburb of Minneapolis. His younger sister, Mary Lucia, is a DJ at local radio station 89.3 The Current.