‘Hamilton’ star Daveed Diggs talks about his taxes
Broadway rapper’s situation offers lessons on tax filing, organization

May 10, 2016

Be still, my heart. Daveed Diggs talked about taxes!

Daveed Diggs talking Hamilton and taxes on Jimmy Fallon Tonight Show

Diggs, one of the Tony-nominated stars of the Broadway smash "Hamilton," was on The Tonight Show with Jimmy Fallon last night. He of course talked about his dual roles as America's favorite fighting Frenchman Lafayette and Thomas Jefferson in Lin-Manuel Miranda's $10 Founding Father musical.

Pre-Broadway jobs: However, just before getting the "Hamilton" parts, the accomplished rapper was at home in Los Angeles and was between gigs. To make ends meet, Diggs delivered catering "in my tore-up Honda Civic … mostly fajitas … at minimum wage, no less."

When he got the offer to be part of the ground-breaking production in New York, Diggs "just didn't show up" for the food delivery job.

Then tax time rolled around.

"I did my taxes hella late," Diggs told Fallon, noting that "I applied for the extension. Like it was all good. Everything by the board, totally legal."

Missing W-2: But as so often happens to many of us, when we finally get around to filing, there's an issue.

"I did my taxes real late and had lost the W-2 that they sent me for the $800 I made while I was working there, so I had to call and get the manager to text me a picture of the thing," Diggs said. "It was like, 'Hey man, I don't know if you remember me. I worked there for a few months and I just stopped coming. Really got to get these taxes done. Do you mind?'"

Even though Diggs probably should have given more formal notice, the restaurant didn't mind. "They were really nice," Diggs said. I'm sure that happens all the time in Hollywood, where everyone is a waiter of sorts waiting for his or her big entertainment break.

Diggs got his W-2 and took care of his Internal Revenue Service requirements.

Working around a missing W-2: Diggs documentation dilemma underscores the importance of setting up a tax organization system. That way you'll have everything you need at your fingertips when filing time arrives.

But the best laid tax plans often go awry. So in case you find yourself in a similar situation — W-2 and tax-wise, not getting plum roles in a Broadway hit — check out these steps to take if you don't get your earnings statement.

Diggs' recounting of his tax situation sounded like he had read my story! OK, that's simply "Hamilton" fangirl wishful thinking. But he did do everything right.

Based on the musical magic I hear every time I listen to the "Hamilton" cast album, which is at least a song or two every day, I'm not surprised Diggs hit all the right tax notes, too.

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Tax Season 2026 Continues!

We made it. Tax Day 2025 is finally over. For most of us. When the filing season started on Jan. 26, millions who were expecting refunds filed immediately. Most of us got our returns to the Internal Revenue Service by April 15. But plenty of taxpayers also got extensions. They are looking at an Oct. 15 filing deadline.

Those procrastinating filers aren’t a problem. In fact, the IRS appreciates taxpayers who take time to fill out their 1040 forms correctly. It also is grateful that tax submissions are spread out a bit, especially now that the IRS is a leaner agency. Processing returns is easier when they arrive throughout the year instead of in massive bunches.

But enough about Uncle Sam’s tax collection issues. The focus now is on all y’all who filed for extensions, giving you another six months to complete your return. Since your new mid-October due date will be here before you know it, let’s get started now on meeting it.

The ol’ blog is here to help you finish up your extended Form 1040. You can start with January’s tax tips page, which has links to the rest of the year’s tips by-month collections. You also can peruse various tax categories for more tailored advice by clicking on the More Tax Posts drop-down menu at the top of this (and every) page.

And to make sure you don’t miss your new filing deadline, the count-down clock below will let you know just how much time you to file by Oct. 15. At the latest.e. (Note: I’m in the Central Time Zone, so adjust accordingly for where you live.)

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