Songfacts®:

• History romanticizes artistic pioneers who drive cultural innovation forward. Just as often, the pioneers themselves get the short end of the stick. Such was the case with Paul Westerberg, and such is the basis of this song.
  
  As frontman for The Replacements from 1979 to 1991 (the duration of the band), Westerberg mashed together genres (namely punk, blues, country, swing, and pop-rock) without sentimentality or concern for the expectations of genre-traditionalists. He also sang openly about his own vulnerability, anxiety, and depression. Musically and lyrically, he was very influential on the grunge and "alternative" scene that dominated '90s music.
  
  Yet, other than having two songs ("Dyslexic Heart" and "Waiting For Somebody") on the 1992 hit film Singles, Westerbeg was largely forgotten by the time grunge kicked in. He never saw the financial windfall we expect artistic trailblazers to experience. So, when Bob Mehr asked him about appearing on a VH1 special in a November 2004 issue of Harp, Westerberg responded:
  
  And then when it got to the point where they wanted to team me with younger artists similar to me I felt a little uncomfortable. I almost felt like, "Why the hell do you need me if you've got a younger, fresher version?" That's what 'How Can You Like Him' is about: "How can you like him better than me?" That's pointed at those pretenders who're supposed to be me.
  
  But I understand, 'cause I liked Neil Young when I was a kid and didn't understand that if there had been no Bob Dylan there would've been no Neil Young.
• Some fans have tied the unnamed "him" in this song to singer-songwriter Ryan Adams (onetime frontman for alt-country band Whiskeytown) because of a strange semi-feud he had with Westerberg in the early 2000s.
  
  Westerberg started the drama by saying that someone should knock out Adams' teeth. Adams didn't appreciate that and told Rolling Stone that he left home "because of things like that" and wouldn't listen to Westerberg's music anymore. Westerberg somewhat backpedaled on his comments, but if there was ever a definitive resolution to the feud, neither Westerberg nor Adams ever told the press about it.