You guys. I’m kinda sorta glad it’s Monday. Officially getting old here.

Garlic Brown Sugar Flank Steak with Chimichurri I howsweeteats.com

It’s not my typical thought at the start of every week, but I’m aching to get back to the grind today and get moving in the kitchen. I’m ready to trash things up with some inappropriate pairings and eat my weight in avocado toast.

Yesterday I spent a large amount of my time flying home from Salt Lake City and it included some bigtime airplane karma in the form of four screaming toddlers behind me on my four hour flight. This is obviously leftover fate and well deserved from that time I was on an airplane with Bev and didn’t shut up for over four hours straight. I get whatever is coming to me in the air. Maybe it has something to do with a theme of fours?

Garlic Brown Sugar Flank Steak with Chimichurri I howsweeteats.com

Now. On to steak.

Well. It’s not really even about the steak… it’s about the sauce.

I’ve been loving on chimichurri ever since the middle of last summer when we ate a dish of the most tender hanger steak covered in the green stuff. It was heavy on the cilantro, so of course I completely loved it and couldn’t recreate it any other way.

If you’re a cilantro hater here, you’ll probably want to cry. The bad news is that this is a super cilantro heavy chimichurri. The good news is that it doesn’t have to be, and you can play around with your own ratio of parsley and cilantro. Deal?

People have very strong emotional reactions to cilantro. I get it. Replace cilantro with fennel seeds and I become your worst nightmare.

Garlic Brown Sugar Flank Steak with Chimichurri I howsweeteats.com

So honestly, the chimichurri has blown my mind.  I don’t think it’s any secret how crazy I am over flank steak, but just how much flavor this gorgeous herby spread stuff adds?! Holy cow. I’m wowed. Enough to rhyme.

The steak too though. We prepare flank steak often, but I wanted to emphasize some sweetness with this version. It sounded so… GOOD – so good with the chimichurri which has a bit of a vinegary tang. And I flip over anything with a vinegary tang. Give me all of the pickles and olives in the universe please.

The flavor of the steak alone was to die for, but WITH the chimichurri? Don’t even know what to do with myself.

I was practically eating the chimichurri with a spoon. Well, I was eating it with a spoon. It goes with everything. Like… a spoon.

My point is that these two things, so seemingly simple, made a huge bang on my plate. So much flavor. So much love. This is the easiest thing ever but you get to do whatever you want with it. Eat it however you’d like. Serve it with potatoes or salads or tortillas or by itself as a snack. Dip the steak into the chimichurri and eat it like pretzels with dip.

I have no idea who would do that last one.

Garlic Brown Sugar Flank Steak with Chimichurri I howsweeteats.com

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Garlic Brown Sugar Flank Steak with Chimichurri

Yield: serves 4 with a lot of extra chimichurri

Prep Time: 2 to 24 hours for marinade

Cook Time: 30 minutes

Ingredients:

2 pound flank steak (about 1-inch thick)
1/2 teaspoon salt
1/2 teaspoon pepper
1/3 cup olive oil
3 tablespoons brown sugar
4 garlic cloves, minced

chimichurri
1 cup fresh cilantro
2/3 cup fresh parsley
1/4 cup fresh oregano
2 garlic cloves, minced
1/4 cup red wine vinegar
2/3 cup olive oil
1/2 teaspoon salt
1/2 teaspoon pepper
1/4 teaspoon crushed red pepper flakes

Directions:

Add the flank steak to a large baking dish and season it with the salt and pepper. In a bowl, whisk together the olive oil, brown sugar and garlic cloves, then cover the steak with it and place it in the fridge to marinate. I marinate anywhere from 2 hours to overnight.

When you're ready to cook the steak, you can grill, broil or pan sear it to your liking. I tend to broil it as I find that easiest. Preheat the broiler in your oven and move the oven rack as close as possible. Place the steak on a broiler pan or baking sheet and broil on each side for about 5 minutes. This will result to a medium to medium-well doneness in my oven.

Allow the steak to rest for 10 minutes before slicing it thinly against the grain. Serve it immediately with the chimichurri.

chimichurri
Combine the parsley, cilantro, oregano and garlic in a food processor and pulse until small leaves and pieces remain. Add in the vinegar and pulse once more. With the processor going, stream in the olive oil and mix until just combined. Stir in the salt, pepper and red pepper flakes. Taste and season additionally if needed. Store sealed in the fridge for up to a week or so.

[sauce adapted from food network

Garlic Brown Sugar Flank Steak with Chimichurri I howsweeteats.com

(okay now I’m over Monday at this point.)

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103 Responses to “Garlic Brown Sugar Flank Steak with Chimichurri.”

  1. #
    51
    Sophia @ NY Foodgasm — January 28, 2014 @ 4:32 pm

    This looks simply AMAZING, MUST have now!

    Reply

  2. #
    52
    Sue — January 28, 2014 @ 8:06 pm

    There’s local Tex Mex restaurant here that serves chimichurri with pasalito’s. But really.. what wouldn’t you want to put it on? Crazy good.

    Reply

  3. #
    53
    Whitney @ The Newlywed Chefs — January 28, 2014 @ 9:58 pm

    Oh this chimichurri looks packed with flavor! And it’s good to know someone else out there eats their weight in avocado toast :)

    Reply

  4. #
    54
    Gina — January 28, 2014 @ 11:51 pm

    The husband always turns up his nose at hanger steak, but he loves chimichurri. Think I could sneak this one past him. Thanks!

    Reply

  5. #
    55
    Ashley @ Our Full Table — January 29, 2014 @ 12:22 am

    In my opinion you could add chimichuri to anything and it would be divine.

    Reply

  6. #
    56
    Cindy Swain — January 29, 2014 @ 5:09 am

    My Italian mother-in-law makes a spread out of parsley that is absolutely delicious. Yours with cilantro though will surely rival hers. LOVE cilantro. I am definitely trying this one!

    Reply

  7. #
    57
    Jennie @themessybakerblog — January 29, 2014 @ 9:54 am

    I had my man child of a husband pester me for an entire 3 hours on our flight to Cancun last week. He can’t sit still to save his life. I’m all about the cilantro, so load me up. This looks so good!

    Reply

  8. #
    58
    Lauren Scott — January 29, 2014 @ 11:38 am

    Made this last night…SO good! Huge hit with the husband. But why oh why does broiling something smoke out my whole house?? My crappy oven that is only a year old?…sigh.

    Reply

  9. #
    59
    ATasteOfMadness — January 29, 2014 @ 1:02 pm

    Oh my goodness, this looks so good! I also love vinegary tang, so this would be perfect for me ;)

    Reply

  10. #
    60
    Alissa — January 29, 2014 @ 1:20 pm

    I have been making this for the past couple of years, but I have never added brown sugar to it. I will be from now on! I LOVE chimichurri, and wish I knew more stuff to add it to. I wish I wasn’t snowed in, because now I really want it!

    Reply

  11. #
    61
    Heather — January 29, 2014 @ 2:32 pm

    This looks ammmmmmazing…but I have a huge cilantro hater on my hands. What do you think substituting arugula for cilantro would be like? I feel like it could work, maybe less than a cup of arugula and more parsley so it’s not too peppery? I want to make this but he will flip his lid over the slightest hint of cilantro flavor!!

    Reply

  12. #
    62
    Lindsay — January 29, 2014 @ 6:36 pm

    Steak and Chimichurri is one of my all time favorite combination! Gorgeous photos!

    Reply

  13. #
    63
    Sylvia — January 30, 2014 @ 10:58 am

    Since we raise a few cows and have a freezer full of beef, I was drawn to this amazing recipe. I think it was calling my name. Ha! I love cilantro and this whole plate appeals to me. Plus, your photos are fabulous!

    Reply

  14. #
    64
    Megan O'Connor — January 30, 2014 @ 1:53 pm

    Think I am going to make a big batch of this and take the Chicago Food Swap. Love the cilantro-heavy version!

    Reply

  15. #
    65
    Kimberly — January 31, 2014 @ 2:02 pm

    I made this last night and it was AMAZING! SO looking forward to the leftovers tonight. Thank you!

    Reply

  16. #
    66
    Janna — January 31, 2014 @ 6:35 pm

    I’ve just discovered your blog. LOVING the recipes. Making lots of things for baby showers and super bowl parties this weekend! And making this for dinner right now!

    Reply

  17. #
    67
    stephanie — January 31, 2014 @ 9:13 pm

    I have never had Chimichurri…does anyone know if this would this be good lightly spread on a pizza and steak strips?

    Reply

  18. #
    68
    Paul — February 2, 2014 @ 12:58 am

    I absolutely love chimichurri! I like to make it with fresh squeezed lime juice instead of the red wine vinegar…really seems to brighten it up even more!

    Reply

  19. #
    69
    Emily @ Life on Food — February 2, 2014 @ 7:51 pm

    Mondays are always so much better with a good meal.

    Reply

  20. #
    70
    Jessica — February 3, 2014 @ 11:39 am

    I have no words. We ate this last night and it was fabulous! Thanks for the recipe – can’t wait to make it again.

    Reply

  21. #
    71
    Laurie — February 3, 2014 @ 5:58 pm

    Seriously, the best flank steak I’ve made. The brown sugar and chimichurri are the perfect paring.

    Reply

  22. #
    72
    Anisah — February 8, 2014 @ 8:31 am

    OMG this sauce! I’ve actually had it with just a spoon because it was that good. We had it with lamb that my husband roasted and it was delicious. Today I was running on low and decided to open a pita bread, fill it with some leftover chicken, sliced onions and this sauce and yummmmyyyy! I am so glad I saved this recipe when I was clearing out my inbox. Thank you!

    Reply

  23. #
    73
    Jessica — February 27, 2014 @ 4:27 pm

    My oven is really old and I am afraid that the broiler won’t get hot enough to cook the steak. What kind of pan do you suggest I use when searing it on the stove top?

    Reply

  24. #
    74
    Teresa — March 12, 2014 @ 1:12 pm

    Absolutely delicious! Made thins last. Ight on the grill. Marinaded flank for 6 hours. So simple . Also made chimichurri which was a great accompaniment to the steak.. Thanks

    Reply

  25. #
    75
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  26. #
    76
    don — August 14, 2014 @ 4:10 pm

    Looks delicious, really like chimichurri, thaks for the great post.

    Reply

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