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‘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!

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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The More Tax Posts tab at the top of this page will take you to, well, more tax posts. You also can search below for a tax topic. 

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TAX-SAVVY WAYS 
TO WRAP UP 2026

It’s over! With October’s extended filing deadline behind us, it is now time to focus on year-end moves to reduce your 2026 tax bill. 

You’ll find ways to do just that on the Tax Tips page (see the More Tax Posts drop-down menu at the top of the blog), as well as the separate tax tip pages for each month, notably October through December. If you’re on the Tax Tips page, you’ll find a monthly list at the end of this column. If you’re on another blog page, you can head straight to the October tips; at the bottom of that tips page you’ll find links to all the other 11 months’ collections of tax advice.

Not to spoil what you’ll find in that tax advice, but it does cover such things as tax deductions for charitable donations, investment moves that could reduce tax due, and ways to max out your tax-favored retirement savings. 

Finally, as the year winds down, things get hectic. There are lots of other things to occupy our time, like the much more fun upcoming holidays. But don’t lose sight of taxes, since timing is key. To be of use, most tax moves must be made by the end of the tax year. That’s Thursday, Dec. 31, which also is the last business day of the year. 

So that you don’t miss that final tax year deadline, also keep an eye on the countdown clock below. It will keep you on top of just how much time is left to make important, tax-saving moves. (Note: I’m in the Central Time Zone, so adjust accordingly for where you live.)

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