Howard Stern is known for being one of the best celebrity interviewers in the entire buinsess. When it comes to getting famous people to part with the most intimate details of their lives, no one is more skilled than Howard. On top of this, Howard's best interviews feel like a healthy balance between a hang-out and a session with a superb shrink. It doesn't matter if he's talking to an A-list actor, a musician, or a politician, the self-proclaimed King Of All Media is a straight-up master at making his guests feel comfortable, energetic and talkative. But Howard's greatest interviews are clear and very well-known, his less than stellar ones, however.... not so much.
While Howard has interviewed countless members of the Wack Pack, callers, and B-list celebrities such as adult movie stars, his worst interviews have tended to be some of the most famous people in the world. Sometimes these are people who have appeared on the show multiple times and have redeemed themselves in the eyes of the audience. Others are one-offs who should stay that way. At least, this is what fans on Reddit claim. Here are Howard's absolute worst celebrity interviews over his 40-year career...
10 Harry Styles In 2020
Everyone has their own opinion about what went down between Howard Stern and Harry Styles in 2020. Some fans think Howard pushed things too far when he asked Harry about his sex life. Others thought Harry was boring and didn't answer questions that other rockstars would be happy to answer. Additionally, Harry resorted to giving Howard three or four-word answers when the radio host was asking about his family life. Regardless of what one may think about the interview, the two just didn't seem to jive.
9 Will Ferrell In 2003
At Howard Stern's Birthday Bash in 2016, the radio legend admitted that he regrets his one and only interview with comedy legend Will Ferrell. While fans on Reddit say that Will had a bit of "chip on his shoulder' throughout the interview, others felt that Howard totally drop the ball. In fact, they claim that Howard was being mean to the Anchorman star. This is an assessment that the King of All Media agrees with.
8 Emily Blunt In 2015
Emily Blunt has been on The Stern Show a couple of times and her more recent appearances are among Stern's best interviews. This is mostly because Howard and Emily have become friends in real life. But her 2015 interview predates that and it contains one of the most awkward moments in his show's history. That would be the time he pretended to be Michael Buble and asked Emily what went wrong in their relationship. Emily wasn't having it and the rest of the interview was equivalent to a very long, uncomfortable pause.
7 Emma Bunton In 2005
Before Howard's evolution as both a man and a radio personality, he made former Spice Girl Emma Bunton extremely uncomfortable while asking her questions about her time in puberty. Some felt that a few of the things Howard said were "sexist", according to Nicki Swift. Others thought it was funny. But Emma was clearly uncomfortable and that made for a bad celebrity interview.
6 Mick Jagger In 2021
While Howard would probably disagree with this entry, Mick was undoubtedly one of the biggest disappointments in Stern Show history. This is because Howard had dreamed about getting The Rolling Stones frontman on his show for years. But when Mick finally came on, it didn't seem too happy to be there. The interview was extremely short and rushed. Mick avoided giving the kind of juicy details that rock icons Sir Paul McCartney and Billy Joel freely share. On top of this, Howard also moved his show to accommodate the morning-avoiding talent. It was a big disappointment.
5 Lindsay Lohan In 2019
Much like Mick Jagger, Lindsay Lohan's appearance was far less exciting than it should have been. The Mean Girls star has lived quite an incredible (and scandalous) life and surely has better stories to share than some advice Jamie Lee Curtis once gave her. While there were certainly strong moments in the interview, it mostly just fell flat. Fans could blame Howard for this, but it really felt as though Lindsay was phoning the whole thing in.
4 Gilda Radner In 1983
In 1983, Howard Stern was one of the scariest names in entertainment. It was near the beginning of his career and he was already known as one of the edgiest shock jocks of all time. This undoubtedly freaked SNL star Gilda Radner out when she appeared on the show in a "Mystery Guest" segment. However, it was Howard's co-host Robin Quivers that pushed Gilda's buttons. The whole thing became less of an interview and more of a... well... complete disaster.
3 Robin Williams In The Early 1990s
The Howard Stern/Robin Williams interview may be historical but it's also one of the radio legend's biggest regrets, according to Page Six. Howard claims that his ego got in the way of really talking to this comedy legend. Even though Howard was actually deeply impressed with Robin and looked up to him, his interview became more about shocking and upsetting the comedian. This isn't dissimilar to how Howard conducted many of his interviews in the 1990s, but this was easily one of his worst.
2 David Arquette In 2013
David Arquette has been a guest on The Howard Stern Show numerous times, but his random phone call interview in 2013 was just a downright mess. According to fans on Reddit and Nicki Swift, this is easily one of Howard's worst interviews of all time. But unlike Robin Williams, this wasn't Howard's fault. David was admittedly "wasted" and made some strange comments about a certain evil dictator. David returned to The Stern Show a couple of years later and got into an argument with Howard about his ex-wife, Courteney Cox, but this was definitely his worst appearance.
1 Dana Plato In 1999
The Different Strokes actor's final interview on The Stern Show In 1999 is brutal. There's no other way to put it. The struggling actor was exposed to the full and wild antics of a 1990s Howard Stern in the interview that happened just one day before her passing. Dana was clearly in a bad state and Howard pushed things WAY too far for a laugh. Fortunately, he's come a long, long, long way since this horrendous interview.
