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Set the Text Type > Create Outlines Draw the rectangle Grab the Shape Builder Tool Hold down the Option/Alt key and click-drag across rectangle
This is now a built-in feature as of 2014 in Adobe Illustrator CC. You'll find it under Type > Area Type Options > Auto Size.
In Photoshop If you're going for a similar style of the original artwork and using Photoshop then you will want to use the Distort Tool. Write out your text. I quickly used the pen tool to show an example of the original text. You have to turn your type layer into a smart object. Right click on the type layer in the layers panel and click Convert to Smart ...
According to the guidelines, 26% opacity is meant for hint text and disabled text. More prominent labels should be 87% black or 54% black depending on whether they are considered primary or secondary text. In the guideline you quoted: Text hints for users, like those in text fields and labels, have an even lower visual prominence and should have an ...
Figured out on my own. Posting it on here for reference: Select textbox Layer > Style > Select Fill Select Pattern Image as Fill type
Type and arrange your text. Apply an Outside Stroke making it bigger and bigger until everything is covered. Mine is rounded because I used a round font, the text in yours is square because its a square font: Select your text layers together and Convert to Smart Object Then Edit > Transform > Perspective and in the same one can do a slight skew: ...
In order to use transparencies with GIMP, you need to add an alpha layer. Check your Image Mode; if you are in Indexed or Grayscale mode, convert to RGB mode. The options for adding alpha layers (RGBA) will then be available. The relevant parts of the documentation are: 4.7. Change the Mode 7.33. Add Alpha Channel
Observing that the EPS file uses PDF-style syntax, I noted that the text scaling is done with Tf: 8 0 0 8 5.327283 18.119995 Tm The 6 numbers are a transformation matrix, where the first number (8) is the x scale and the fourth number (also, as it happens, 8) is the y scale of the text. You have to pick one (well, usually) – I picked the first number. ...
Make sure the rectangle is behind the type (that has been converted to outlines). Then try the Pathfinder tool: Minus Back.
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