Ted struggles to fire an employee. Meanwhile, Barney and Robin find an old nude portrait of Marshall that Lily painted, which prompts Barney to hire Lily to paint him.
Ted decides to fire his former boss, Hammond Druthers, who is always ridiculing the ideas for the building. The first time Ted tries to fire him, he is stopped when his coworkers throw a surprise party for Druthers. When Ted comes to his office later that night, he finds Druthers sleeping in the office since his wife threw him out. Ted tries to fire him again but ends up taking Druthers to the apartment, letting him sleep on the couch.
Next day, Druthers thanks Ted for letting him stay with him, but still ridicules his ideas in front of others. When Ted tries to fire Druthers the third time, he gets divorce papers from his wife, also telling him that their dog died. When Ted tries to fire him anyways, a few coworkers approach them and shout "Happy Birthday" to Druthers since they missed the party as they were in Montreal. Just then he appears to be suffering from a heart attack, but thinking that he is faking it, Ted fires him anyways. However, Ted's coworkers start to hate him when they it turns out that Druthers really did have a heart attack. Later, Ted gets a margarita machine for the office, and everyone forgives him.
Barney finds a nude painting of Marshall at the apartment, and shows it to Ted and Robin. When they show it to Marshall and Lily, Future Ted explains that Lily painted it back in Wesleyan, because Marshall was uncomfortable with Lily painting another guy naked for her art class. To annoy Marshall, Barney hangs the painting at MacLaren's, but Marshall steals it later on.
At the bar, when Lily and Barney are alone, Barney praises Lily's work, and asks her to paint him nude for $5,000. Lily tells him she will think about it and discusses it with Marshall, saying that they will be able to spend their honeymoon in Scotland, near the Loch Ness Monster. Marshall agrees, but later stops Lily when she is painting Barney. He tells her privately that they could live in a castle for another $2,000, but shows to Barney that he doesn't want Lily painting him naked. Barney offers them another $5,000. When Lily is done painting Barney, she quickly leaves with Marshall, and Barney complaining that she didn't paint his genitals when they leave.
Ted mentions having been promoted to head architect of the project in Atlantic City, which happened after he showed his design to the Spokane National Bank executives in Aldrin Justice.
In Sorry, Bro, Ted accuses Lily of only hating his college girlfriend Karen because she walked in on her painting Marshall nude and ogled him.
Lily explains, in Sorry, Bro, that she had to paint Marshall nude because he ate her bowl of fruit.
Hammond Druthers later becomes a "key player" at an architecture firm in Chicago, as revealed in Platonish, where a flashback shows him attempting to convince Ted to come work for him, which, as revealed in Something New, he eventually agrees to.
(trying to sleep) Do whatever you want to me, just don't wake me up...
Hey, guys! Guess what I got? A new dart!
Oh wow, a new dart!
Hey, that new dart is great!
I did not know you were such a fan of "new dart", Barney!
Oh yes, Robin, I just love "nude art"...”nude art"...[after an awkward stare from Marshall] "nude art"! [laughs]
You found the painting, didn't you?
(trying to paint Barney with a sword in his hand) I don't think your sword will fit.
I get that a lot.
Oh my God!!
Do you know about this?
What is that?
Only the greatest thing ever! Shh, wait, wait, wait that's not enough build-up... If they were to cure cancer tomorrow, this would still be the greatest thing to happen all week. Ok, now you're ready... for Naked Marshall(Shows Marshall's naked painting).
Wait. If Marshall went to all this trouble to hide it he clearly doesn't want us to find it.
Oh, come on. Robin?
No! I'm saying that he must be really embarrassed by this... We're gonna have so much fun!!
(seeing his nude painting) A smooth area?! You gave me the Ken doll?! She left out Little Barney! Barnacle Jr...my Barnana is...Barnito Supreme....
You have been blessed with a wonderful gift.
I meant me.
(after watching Marshall steal his nude painting from the bar) One of my worst fears just came true- I saw Marshall grab himself naked.
(about Marshall's nude painting) I knew this day would come.
How did you know that?
Because I didn't hide it very well.
(about his boss) Did you see what he was wearing today? It was like his pants were being held up by his nipples.
In my body, where the shame gland should be, there is
a second awesome gland. True story.
Notes and Trivia
Goofs and Errors
In this episode Lily explains that she painted Marshall nude for her art class, but in Sorry, Bro she says that it's because he ate her bowl of fruit. Both could be true if Lily planned to paint her bowl of fruit for art class.
During the scene in the office where Druthers and Ted are drinking together, the position of the liquor bottle changes and then changes back.
When Karen makes her appearance in the series, Ted says that Lily hates her because she (Karen) lingered while she (Lily) was painting Marshall. However, in this episode it appears as though Ted sees the painting for the first time. It's possible that Lily told Ted about Karen lingering sometime between this episode and Karen's appearance on the show.
In Miracles, when Lily calls Barney, he says that Robin told her what's under the hood and she wants to take it for a spin but Lily has already seen Barney naked in this episode.
Allusions and Outside References
Marshall tells Ted to ask himself Who's the Boss?, a reference to the 80s TV show. Barney is the only one who answers Mona.
Ted references the alternative rock band Foo Fighters during several flashbacks.
Marshall's concern about what Lily had to do to get the money, alludes to the 1993 movie Indecent Proposal.
In the Wesleyan scene where Lily proposes to Marshall about the nude painting, Marshall is seen playing Super Mario World.
In the scene where Ted finds out Druthers is sleeping at his office, they both drink from a bottle labelled "J. Buckley," a reference to the singer Jeff Buckley.