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. #
    1
    Taylor @ FoodFaithFitness — January 27, 2014 @ 8:10 am

    I had chimichurri in Mexico for the first time last year and fell in love….yes, it definitely goes VERY well with a spoon. And my face. And this steak. And….yum.

    Reply

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    2
    Belinda@themoonblushbaker — January 27, 2014 @ 8:12 am

    Nope I am a full Cilantro lover, in fact have been known to use it as salad vegetable rather than herb. I must hear more about your trip; even though the plane ride sucked I am sure this steak could fix all toddler trouble wounds.

    That last picture is gold!

    Reply

    • Jessica — January 27th, 2014 @ 9:09 pm

      i’ve also used it as a base in salads… love it!

      Reply

  3. #
    3
    DessertForTwo — January 27, 2014 @ 8:25 am

    gah! My death bed meal. I adore cilantro. It runs in the family. My uncle and I made cilantro ice cream once. Yeah. I want to wear perfume that smells like cilantro.

    Reply

  4. #
    4
    Laura (Blogging Over Thyme) — January 27, 2014 @ 8:56 am

    I’m not with you on the excitement for Monday. BUT this steak? Yes. Especially with all of the cilantro in the chimichurri. I’ve always been “eh” about chimichurri sauce, but clearly I just need to replace the parsley with more cilantro.

    I want to slather some on my eggs this morning!

    Reply

  5. #
    5
    Alicia Greenrabbit — January 27, 2014 @ 9:01 am

    I don’t know ,not liking Cilantro is like ,not liking chocolate or garlic ,but not together……?
    You never know these day with all the mixing of sweet ,salty and sour foods.
    I think I can get my husband ( Mr. meat & potato man ) to eat this on his steak, forget the gravy.

    Reply

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    Cara's Healthy Cravings — January 27, 2014 @ 9:05 am

    Beauty food styling!
    Looks mouth-watering good.

    Reply

    • Jessica — January 27th, 2014 @ 9:08 pm

      thanks!

      Reply

  7. #
    7
    Brie @ Entrée the Giant — January 27, 2014 @ 9:07 am

    The older I get, the more a$$ backward my week becomes – I am starting to love Sunday nights/Monday mornings. Going to bed early, getting back to a routine, etc.

    The younger, cooler version of me is completely ashamed.

    Reply

    • Jessica — January 27th, 2014 @ 9:09 pm

      I FEEL YOU.

      Reply

  8. #
    8
    Liz @ Tip Top Shape — January 27, 2014 @ 9:16 am

    This looks great!! I’m not a big cilantro fan, but I usually like chimichurri. I feel like that’s a bit backwards – but hey, I’m not questioning my tastebuds!

    Thanks for sharing :)

    Reply

  9. #
    9
    Madison — January 27, 2014 @ 9:26 am

    Amazing, fresh and spicy all in one dish. Come to MAMA!

    Reply

  10. #
    10
    Kim in MD — January 27, 2014 @ 9:29 am

    Yay for Monday! This looks incredible!

    Reply

  11. #
    11
    Karly — January 27, 2014 @ 9:40 am

    I officially love Mondays now if it means I get to stare at and drool over things like this! Gorgeous!

    Reply

  12. #
    12
    Liz @ The Lemon Bowl — January 27, 2014 @ 9:44 am

    I want to live in that chimichurri.

    Reply

    • Jessica — January 27th, 2014 @ 9:09 pm

      roommates!

      Reply

  13. #
    13
    Amy @ whatsbakingbaby — January 27, 2014 @ 9:51 am

    Thanks for making me want a steak at 9 am :)

    Reply

  14. #
    14
    Ashley — January 27, 2014 @ 9:52 am

    I love the color contrast and shadows in these photos. I am also ready for + so over Monday at the very same time. Here’s to a productive week!

    Reply

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    15
    Rachel — January 27, 2014 @ 10:01 am

    I have been obsessed with making a chimichurri steak since my date ordered it the other week and I could not stop stealing bites. Then my friend Rose blogged a recipe with a great salad with charred corn on the side (http://www.thelondoner.me/2014/01/chimichurri-t-bone-blackened-corn-salad.html) so now I have to think that I need to make her salad and your steak and sauce, because I am a cilantro worshiper. I used to hate the stuff, then I was totally converted. Now I can’t get enough of it!

    Your photos are flawless, as ever, by the way.

    Reply

    • Jessica — January 27th, 2014 @ 9:08 pm

      thank you! and that salad sounds insanely delish.

      Reply

  16. #
    16
    Sophie — January 27, 2014 @ 10:04 am

    Oh gosh this looks so yummy, have bookmarked the recipe :)

    Sophie
    http://what-sophie-said.blogspot.co.uk/
    xxx

    Reply

  17. #
    17
    Tieghan Gerard — January 27, 2014 @ 10:09 am

    I love the cilantro and most of the time I love Mondays too. Just not this Monday. Ugh. it has been bad before it even started….long story.

    Anyway, this make it better. Chimichurri is the best!

    Reply

  18. #
    18
    betty — January 27, 2014 @ 10:26 am

    you lost me at a cup of cilantro.. but i’d def love to try flank steak. flank has been in my rotation often these days.. love it!

    Reply

  19. #
    19
    RavieNomNoms — January 27, 2014 @ 10:26 am

    Holy flank steak Batman! That looks outstanding!

    Reply

  20. #
    20
    Bri — January 27, 2014 @ 10:28 am

    I love chimichuri! thanks for sharing! I can’t wait to try it.

    Reply

  21. #
    21
    Erin | The Law Student's Wife — January 27, 2014 @ 10:57 am

    I think this week at lunch, I’m going to pack an entire container of this chimichurri and suck it down with a straw. Let my coworkers stare. I know it’s because they are jealous!

    Reply

  22. #
    22
    Christine @ Cooking with Cakes — January 27, 2014 @ 10:57 am

    I dig cilantro, so I’m cool with this. You and I have a mushrooms divide, but I’m moving passed it ;) lol

    Reply

  23. #
    23
    Jessica @ Food Luv Bites — January 27, 2014 @ 10:59 am

    Yummy, this looks amazingly delicious.

    Reply

  24. #
    24
    Nicole ~ Cooking for Keeps — January 27, 2014 @ 11:48 am

    I’m in the obsessed with cilantro camp, so this is seriously up my alley. GORGEOUS colors!

    Reply

  25. #
    25
    Jamie @ Dishing Out Health — January 27, 2014 @ 11:55 am

    This is one of my favorite combinations! I’ve actually been lovin’ chimichurri on breakfast scrambles too :P

    Reply

    • Jessica — January 27th, 2014 @ 9:07 pm

      so gonna try that.

      Reply

  26. #
    26
    natalie @ wee eats — January 27, 2014 @ 12:54 pm

    This is perfect because the only chimichurri I had was SUPER HEAVY on parsley and I was NOT a fan. But cilantro? Now that’s something I can get behind. And I’m SO WITH YOU on the fennel seeds (yuck.)

    Reply

    • Jessica — January 27th, 2014 @ 9:06 pm

      i can’t deal with heavy parsley either. i get it!

      Reply

  27. #
    27
    Kelli @ The Corner Kitchen — January 27, 2014 @ 1:37 pm

    Yes to flank steak. Yessss to cilantro. And, absolutely, positively YES to chimichurri!!

    Love the photos, btw!!

    Reply

  28. #
    28
    HeatherChristo — January 27, 2014 @ 1:42 pm

    I love chimichurri!! this whole dish is gorgeous. I sat next to a child that screamed for 4 hours on Friday- my sympathies…

    Reply

  29. #
    29
    3girls1apple — January 27, 2014 @ 1:44 pm

    Chimichurri is the best when it comes to churrasco or as some may call flank steak. The 2 go hand in hand. It’s so delicious. Thanks for sharing the recipe from 3girls1apple.com

    Reply

  30. #
    30
    Tereza — January 27, 2014 @ 2:36 pm

    Great way to make a steak dinner extra special! Love the way it adds colour and flavour to a dish.

    http://lfeandcity.tumblr.com

    Reply

  31. #
    31
    Aishah @ Coffee, Love, Health — January 27, 2014 @ 3:30 pm

    I’m such a sauce lover- that sounds so good!!

    Reply

  32. #
    32
    Larry — January 27, 2014 @ 4:25 pm

    Bommmmmb! This looks so effing good that the backs of my cheeks are now salivating. Specifically the backs of my cheeks (it’s the chunkiest part).

    Reply

    • Jessica — January 27th, 2014 @ 9:06 pm

      omg. haha.

      Reply

  33. #
    33
    Angelyn @ Everyday Desserts — January 27, 2014 @ 4:29 pm

    I kinda sorta like Mondays too. But I like this dish more because it looks amazing!!

    Reply

  34. #
    34
    dervla @ the curator — January 27, 2014 @ 4:41 pm

    that steak is calling to me right now … i want to face plant right into it. And CILANTRO = always yes.

    Reply

  35. #
    35
    Kelly @ Laughter, Strength, and Food — January 27, 2014 @ 5:15 pm

    I don’t like steak but this makes me want to love it!!! I think I may just have to give it another shot!

    Reply

  36. #
    36
    Corbin (Decor-Eat) — January 27, 2014 @ 6:43 pm

    Um, yum!! This looks delicious. I had a meal like this at a thai restaurant. It was amazing. I’ll need to try making this at home.

    Corbin

    Reply

  37. #
    37
    Laura (Tutti Dolci) — January 27, 2014 @ 7:42 pm

    Love that marinade and vibrant chimichurri!

    Reply

  38. #
    38
    Amy — January 27, 2014 @ 8:53 pm

    Not a steak eater, but I can see this adapted deliciously for veggie tastes like mine if served over grilled zucchini and mushrooms and roasted sweet potato. The boyfriend can have all the steak to himself that way :)

    Reply

  39. #
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    Happy Valley Chow — January 27, 2014 @ 9:13 pm

    I love chimichurri, it has such a fantastic and fresh flavor. Great job :)

    Happy Blogging!
    Happy Valley Chow

    Reply

  40. #
    40
    Jenna — January 27, 2014 @ 9:32 pm

    Oh my word this looks stunningly good!! I love the vibrant green color the chimuchurri adds! Awesome dinner

    Reply

  41. #
    41
    Mariah and Coty@quirksandtwists — January 27, 2014 @ 10:31 pm

    This looks relish! Love the super green class of the chimichurri!

    Reply

  42. #
    42
    Felicakes — January 28, 2014 @ 1:13 am

    I had Chimichurri for the first time last year and man I was hooked. Now everytime we have a BBQ, I make a batch to marinade the meat and also to eat with the meat!

    Reply

  43. #
    43
    Crystal S. — January 28, 2014 @ 1:46 am

    Mmmm! Chimichurri & steak – sounds great! But chimichurri and brown sugar steak – shed a tear delicious!

    Reply

  44. #
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    Sevimin Askanasi — January 28, 2014 @ 4:54 am

    It seems very hearty, delicious

    Reply

  45. #
    45
    Tracy | Peanut Butter And Onion — January 28, 2014 @ 8:32 am

    I have never been a cilantro fan, but lady you have never steered me wrong, I’ll give it a try

    Reply

  46. #
    46
    Shelley — January 28, 2014 @ 9:04 am

    I’m the same way – love cilantro, loathe fennel. Speaking of loving all things with a vinegary tang (my husband’s nickname for me, btw, is Pickle), hopefully you saw this recipe yesterday from Spoon Fork Bacon, I’m dying to try it soon!:
    http://www.spoonforkbacon.com/2014/01/slow-cooker-pickled-pulled-pork-sandwiches/

    -Side note/question: any suggestions for a substitution for the adobo sauce used in the chipotle crema w/ your grilled corn, mushroom, + roasted poblano tacos I’m making tonight? Apparently, our town doesn’t care for chipotles, @ Trader Joe’s or Kroger. :(

    Reply

    • Jessica — January 28th, 2014 @ 9:44 am

      you can probably try another hot sauce! look for one with a slightly thicker consistency? or if you can find some sort of sweet hot sauce?

      Reply

      • Shelley — January 28th, 2014 @ 10:17 am

        Perhaps I’ll do a little mash-up of our favorite sweet + smoky BBQ sauce (for the thickness) + our favorite hot sauce! Thanks!

  47. #
    47
    Mimi — January 28, 2014 @ 9:54 am

    Funny. I just made the same dinner! Not on my blog, but the chimichurri is! Such good stuff!

    Reply

  48. #
    48
    Melissa @ Treats With a Twist — January 28, 2014 @ 11:01 am

    OMG I’m totally the same way about cilantro and fennel. If I wanted black licorice, I wouldn’t have picked out all the black jelly beans and tossed them in the trash for all these years. Not. A. Fan.
    This, however. Gah it looks so good. This would make some amazing tacos…or be good on a bed of spaghetti squash…or on a Brussels salad! Holy yum!

    Reply

  49. #
    49
    collette — January 28, 2014 @ 2:23 pm

    I have 15 pounds of flank steak in my freezer….. CAN.NOT.WAIT to make this!!

    Reply

  50. #
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    aida mollenkamp — January 28, 2014 @ 4:24 pm

    I love a good chimichurri — something so satisfying about it!

    Reply

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