diff --git a/src/wily/__main__.py b/src/wily/__main__.py
index 067f643..377c7c8 100644
--- a/src/wily/__main__.py
+++ b/src/wily/__main__.py
@@ -154,7 +154,13 @@ def build(ctx, max_revisions, targets, operators, archiver):
 @click.option(
     "-m", "--message/--no-message", default=False, help=_("Include revision message")
 )
-def index(ctx, message):
+@click.option(
+    "-w",
+    "--wrap/--no-wrap",
+    default=True,
+    help=_("Wrap index text to fit in terminal"),
+)
+def index(ctx, message, wrap):
     """Show the history archive in the .wily/ folder."""
     config = ctx.obj["CONFIG"]
 
@@ -163,7 +169,7 @@ def index(ctx, message):
 
     from wily.commands.index import index
 
-    index(config=config, include_message=message)
+    index(config=config, include_message=message, wrap=wrap)
 
 
 @cli.command(
@@ -206,8 +212,14 @@ def index(ctx, message):
     help=_("Return a non-zero exit code under the specified threshold"),
     type=click.INT,
 )
+@click.option(
+    "-w",
+    "--wrap/--no-wrap",
+    default=True,
+    help=_("Wrap rank text to fit in terminal"),
+)
 @click.pass_context
-def rank(ctx, path, metric, revision, limit, desc, threshold):
+def rank(ctx, path, metric, revision, limit, desc, threshold, wrap):
     """Rank files, methods and functions in order of any metrics, e.g. complexity."""
     config = ctx.obj["CONFIG"]
 
@@ -225,6 +237,7 @@ def rank(ctx, path, metric, revision, limit, desc, threshold):
         limit=limit,
         threshold=threshold,
         descending=desc,
+        wrap=wrap,
     )
 
 
@@ -260,9 +273,15 @@ def rank(ctx, path, metric, revision, limit, desc, threshold):
     default=False,
     help=_("Only show revisions that have changes"),
 )
+@click.option(
+    "-w",
+    "--wrap/--no-wrap",
+    default=True,
+    help=_("Wrap report text to fit in terminal"),
+)
 @click.pass_context
 def report(
-    ctx, file, metrics, number, message, format, console_format, output, changes
+    ctx, file, metrics, number, message, format, console_format, output, changes, wrap
 ):
     """Show metrics for a given file."""
     config = ctx.obj["CONFIG"]
@@ -297,6 +316,7 @@ def report(
         format=ReportFormat[format],
         console_format=style,
         changes_only=changes,
+        wrap=wrap,
     )
 
 
@@ -322,8 +342,14 @@ def report(
 @click.option(
     "-r", "--revision", help=_("Compare against specific revision"), type=click.STRING
 )
+@click.option(
+    "-w",
+    "--wrap/--no-wrap",
+    default=True,
+    help=_("Wrap diff text to fit in terminal"),
+)
 @click.pass_context
-def diff(ctx, files, metrics, all, detail, revision):
+def diff(ctx, files, metrics, all, detail, revision, wrap):
     """Show the differences in metrics for each file."""
     config = ctx.obj["CONFIG"]
 
@@ -347,6 +373,7 @@ def diff(ctx, files, metrics, all, detail, revision):
         changes_only=not all,
         detail=detail,
         revision=revision,
+        wrap=wrap,
     )
 
 
@@ -432,8 +459,14 @@ def clean(ctx, yes):
 
 
 @cli.command("list-metrics", help=_("""List the available metrics."""))
+@click.option(
+    "-w",
+    "--wrap/--no-wrap",
+    default=True,
+    help=_("Wrap metrics text to fit in terminal"),
+)
 @click.pass_context
-def list_metrics(ctx):
+def list_metrics(ctx, wrap):
     """List the available metrics."""
     config = ctx.obj["CONFIG"]
 
@@ -442,7 +475,7 @@ def list_metrics(ctx):
 
     from wily.commands.list_metrics import list_metrics
 
-    list_metrics()
+    list_metrics(wrap)
 
 
 @cli.command("setup", help=_("""Run a guided setup to build the wily cache."""))
diff --git a/src/wily/commands/diff.py b/src/wily/commands/diff.py
index fc19c6f..ec0768b 100644
--- a/src/wily/commands/diff.py
+++ b/src/wily/commands/diff.py
@@ -15,7 +15,7 @@ from wily import format_date, format_revision, logger
 from wily.archivers import resolve_archiver
 from wily.commands.build import run_operator
 from wily.config import DEFAULT_PATH
-from wily.helper import get_style
+from wily.helper import get_maxcolwidth, get_style
 from wily.operators import (
     BAD_COLORS,
     GOOD_COLORS,
@@ -27,7 +27,9 @@ from wily.operators import (
 from wily.state import State
 
 
-def diff(config, files, metrics, changes_only=True, detail=True, revision=None):
+def diff(
+    config, files, metrics, changes_only=True, detail=True, revision=None, wrap=False
+):
     """
     Show the differences in metrics for each of the files.
 
@@ -161,8 +163,15 @@ def diff(config, files, metrics, changes_only=True, detail=True, revision=None):
     descriptions = [metric.description for operator, metric in metrics]
     headers = ("File", *descriptions)
     if len(results) > 0:
+        maxcolwidth = get_maxcolwidth(headers, wrap)
         style = get_style()
         print(
             # But it still makes more sense to show the newest at the top, so reverse again
-            tabulate.tabulate(headers=headers, tabular_data=results, tablefmt=style)
+            tabulate.tabulate(
+                headers=headers,
+                tabular_data=results,
+                tablefmt=style,
+                maxcolwidths=maxcolwidth,
+                maxheadercolwidths=maxcolwidth,
+            )
         )
diff --git a/src/wily/commands/index.py b/src/wily/commands/index.py
index e7f1a55..d8bebc9 100644
--- a/src/wily/commands/index.py
+++ b/src/wily/commands/index.py
@@ -6,11 +6,11 @@ Print information about the wily cache and what is in the index.
 import tabulate
 
 from wily import MAX_MESSAGE_WIDTH, format_date, format_revision, logger
-from wily.helper import get_style
+from wily.helper import get_maxcolwidth, get_style
 from wily.state import State
 
 
-def index(config, include_message=False):
+def index(config, include_message=False, wrap=False):
     """
     Show information about the cache and runtime.
 
@@ -54,6 +54,14 @@ def index(config, include_message=False):
         headers = ("Revision", "Author", "Message", "Date")
     else:
         headers = ("Revision", "Author", "Date")
-
+    maxcolwidth = get_maxcolwidth(headers, wrap)
     style = get_style()
-    print(tabulate.tabulate(headers=headers, tabular_data=data, tablefmt=style))
+    print(
+        tabulate.tabulate(
+            headers=headers,
+            tabular_data=data,
+            tablefmt=style,
+            maxcolwidths=maxcolwidth,
+            maxheadercolwidths=maxcolwidth,
+        )
+    )
diff --git a/src/wily/commands/list_metrics.py b/src/wily/commands/list_metrics.py
index d9b81d1..572b0ee 100644
--- a/src/wily/commands/list_metrics.py
+++ b/src/wily/commands/list_metrics.py
@@ -5,20 +5,24 @@ TODO : Only show metrics for the operators that the cache has?
 """
 import tabulate
 
-from wily.helper import get_style
+from wily.helper import get_maxcolwidth, get_style
 from wily.operators import ALL_OPERATORS
 
 
-def list_metrics():
+def list_metrics(wrap):
     """List metrics available."""
+    headers = ("Name", "Description", "Type", "Measure", "Aggregate")
+    maxcolwidth = get_maxcolwidth(headers, wrap)
     style = get_style()
     for name, operator in ALL_OPERATORS.items():
         print(f"{name} operator:")
         if len(operator.cls.metrics) > 0:
             print(
                 tabulate.tabulate(
-                    headers=("Name", "Description", "Type"),
+                    headers=headers,
                     tabular_data=operator.cls.metrics,
                     tablefmt=style,
+                    maxcolwidths=maxcolwidth,
+                    maxheadercolwidths=maxcolwidth,
                 )
             )
diff --git a/src/wily/commands/rank.py b/src/wily/commands/rank.py
index 29c63cf..8f11710 100644
--- a/src/wily/commands/rank.py
+++ b/src/wily/commands/rank.py
@@ -18,12 +18,12 @@ import tabulate
 from wily import format_date, format_revision, logger
 from wily.archivers import resolve_archiver
 from wily.config import DEFAULT_PATH
-from wily.helper import get_style
+from wily.helper import get_maxcolwidth, get_style
 from wily.operators import resolve_metric_as_tuple
 from wily.state import State
 
 
-def rank(config, path, metric, revision_index, limit, threshold, descending):
+def rank(config, path, metric, revision_index, limit, threshold, descending, wrap):
     """
     Rank command ordering files, methods or functions using metrics.
 
@@ -121,8 +121,17 @@ def rank(config, path, metric, revision_index, limit, threshold, descending):
     data.append(["Total", total])
 
     headers = ("File", metric.description)
+    maxcolwidth = get_maxcolwidth(headers, wrap)
     style = get_style()
-    print(tabulate.tabulate(headers=headers, tabular_data=data, tablefmt=style))
+    print(
+        tabulate.tabulate(
+            headers=headers,
+            tabular_data=data,
+            tablefmt=style,
+            maxcolwidths=maxcolwidth,
+            maxheadercolwidths=maxcolwidth,
+        )
+    )
 
     if threshold and total < threshold:
         logger.error(
diff --git a/src/wily/commands/report.py b/src/wily/commands/report.py
index 2dd0bfa..50a99ea 100644
--- a/src/wily/commands/report.py
+++ b/src/wily/commands/report.py
@@ -11,6 +11,7 @@ from string import Template
 import tabulate
 
 from wily import MAX_MESSAGE_WIDTH, format_date, format_revision, logger
+from wily.helper import get_maxcolwidth
 from wily.helper.custom_enums import ReportFormat
 from wily.lang import _
 from wily.operators import MetricType, resolve_metric_as_tuple
@@ -31,6 +32,7 @@ def report(
     format=ReportFormat.CONSOLE,
     console_format=None,
     changes_only=False,
+    wrap=False,
 ):
     """
     Show metrics for a given file.
@@ -211,8 +213,13 @@ def report(
 
         logger.info(f"wily report was saved to {report_path}")
     else:
+        maxcolwidth = get_maxcolwidth(headers, wrap)
         print(
             tabulate.tabulate(
-                headers=headers, tabular_data=data[::-1], tablefmt=console_format
+                headers=headers,
+                tabular_data=data[::-1],
+                tablefmt=console_format,
+                maxcolwidths=maxcolwidth,
+                maxheadercolwidths=maxcolwidth,
             )
         )
diff --git a/src/wily/helper/__init__.py b/src/wily/helper/__init__.py
index 7c52235..d8c8347 100644
--- a/src/wily/helper/__init__.py
+++ b/src/wily/helper/__init__.py
@@ -1,9 +1,26 @@
 """Helper package for wily."""
+import shutil
 import sys
 
 from wily.config import DEFAULT_GRID_STYLE
 
 
+def get_maxcolwidth(headers, wrap=True):
+    """Calculate the maximum column width for a given terminal width."""
+    if not wrap:
+        return
+    width = shutil.get_terminal_size()[0]
+    columns = len(headers)
+    if width < 80:
+        padding = columns + 2
+    elif width < 120:
+        padding = columns - 2
+    else:
+        padding = columns - 4
+    maxcolwidth = (width // columns) - padding
+    return max(maxcolwidth, 1)
+
+
 def get_style(style=DEFAULT_GRID_STYLE):
     """Select the tablefmt style for tabulate according to what sys.stdout can handle."""
     if style == DEFAULT_GRID_STYLE:

diff --git a/test/integration/test_diff.py b/test/integration/test_diff.py
index 102d31a..2d1760d 100644
--- a/test/integration/test_diff.py
+++ b/test/integration/test_diff.py
@@ -45,6 +45,18 @@ def test_diff_output_all(builddir):
     assert "test.py" in result.stdout
 
 
+def test_diff_output_all_wrapped(builddir):
+    """Test the diff feature with wrapping"""
+    runner = CliRunner()
+    result = runner.invoke(
+        main.cli,
+        ["--debug", "--path", builddir, "diff", _path, "--all", "--wrap"],
+        catch_exceptions=False,
+    )
+    assert result.exit_code == 0, result.stdout
+    assert "test.py" in result.stdout
+
+
 def test_diff_output_bad_path(builddir):
     """Test the diff feature with no changes"""
     runner = CliRunner()
diff --git a/test/integration/test_index.py b/test/integration/test_index.py
index 2d9cad8..1146565 100644
--- a/test/integration/test_index.py
+++ b/test/integration/test_index.py
@@ -34,3 +34,18 @@ def test_index_with_messages(builddir):
     assert "add line" in result.stdout
     assert "remove line" in result.stdout
     assert result.exit_code == 0, result.stdout
+
+
+def test_index_with_messages_wrapped(builddir):
+    """
+    Test that index works with a build with git commit messages and wrapping
+    """
+    runner = CliRunner()
+    result = runner.invoke(
+        main.cli, ["--path", builddir, "index", "--message", "--wrap"]
+    )
+    assert result.stdout.count("An author") == 3
+    assert "basic test" in result.stdout
+    assert "add line" in result.stdout
+    assert "remove line" in result.stdout
+    assert result.exit_code == 0, result.stdout
diff --git a/test/integration/test_list_metrics.py b/test/integration/test_list_metrics.py
new file mode 100644
index 0000000..660b3ab
--- /dev/null
+++ b/test/integration/test_list_metrics.py
@@ -0,0 +1,32 @@
+from click.testing import CliRunner
+
+import wily.__main__ as main
+
+
+def test_list_metrics(builddir):
+    """
+    Test that list-metrics works and is ordered
+    """
+    runner = CliRunner()
+    result = runner.invoke(main.cli, ["list-metrics"])
+    assert result.stdout.count("operator") == 4
+    assert "cyclomatic" in result.stdout
+    assert "maintainability" in result.stdout
+    assert "raw" in result.stdout
+    assert "halstead" in result.stdout
+    # Test ordering
+    i = result.stdout.index
+    assert i("cyclomatic") < i("maintainability") < i("raw") < i("halstead")
+
+
+def test_list_metrics_wrapped(builddir):
+    """
+    Test that list-metrics works with wrapping
+    """
+    runner = CliRunner()
+    result = runner.invoke(main.cli, ["list-metrics", "--wrap"])
+    assert result.stdout.count("operator") == 4
+    assert "cyclomatic" in result.stdout
+    assert "maintainability" in result.stdout
+    assert "raw" in result.stdout
+    assert "halstead" in result.stdout
diff --git a/test/integration/test_rank.py b/test/integration/test_rank.py
index fe62e13..5e852df 100644
--- a/test/integration/test_rank.py
+++ b/test/integration/test_rank.py
@@ -18,6 +18,15 @@ def test_rank_single_file_default_metric(builddir):
     assert result.exit_code == 0, result.stdout
 
 
+def test_rank_single_file_default_metric_wrapped(builddir):
+    """Test the rank feature with default metric and wrapping"""
+    runner = CliRunner()
+    result = runner.invoke(
+        main.cli, ["--path", builddir, "rank", "--wrap", "src/test.py"]
+    )
+    assert result.exit_code == 0, result.stdout
+
+
 def test_rank_directory_default_metric(builddir):
     """Test the rank feature with default (AimLow) metric on a directory"""
     runner = CliRunner()
diff --git a/test/integration/test_report.py b/test/integration/test_report.py
index c5fa049..082ca4d 100644
--- a/test/integration/test_report.py
+++ b/test/integration/test_report.py
@@ -139,6 +139,18 @@ def test_report_high_metric(builddir):
     assert "Not found" not in result.stdout
 
 
+def test_report_wrapped(builddir):
+    """
+    Test that report works with wrapping
+    """
+    runner = CliRunner()
+    result = runner.invoke(
+        main.cli, ["--path", builddir, "report", "--wrap", _path, "raw.comments"]
+    )
+    assert result.exit_code == 0, result.stdout
+    assert "Not found" not in result.stdout
+
+
 def test_report_short_metric(builddir):
     """
     Test that report works with a build on shorthand metric
diff --git a/test/unit/test_helper.py b/test/unit/test_helper.py
index 6b29d3a..8e64f55 100644
--- a/test/unit/test_helper.py
+++ b/test/unit/test_helper.py
@@ -1,8 +1,133 @@
 from io import BytesIO, TextIOWrapper
 from unittest import mock
 
+import tabulate
+
 from wily.config import DEFAULT_GRID_STYLE
-from wily.helper import get_style
+from wily.helper import get_maxcolwidth, get_style
+
+SHORT_DATA = [list("abcdefgh"), list("abcdefgh")]
+
+MEDIUM_DATA = [["medium_data"] * 2, ["medium_data"] * 2]
+
+LONG_DATA = [["long_data"] * 8, ["long_data"] * 8]
+
+HUGE_DATA = [["huge_data"] * 18, ["huge_data"] * 18]
+
+LONG_LINE_MEDIUM_DATA = [
+    ["long_line_for_some_medium_data"] * 2,
+    ["long_line_for_some_medium_data"] * 2,
+]
+
+
+def test_get_maxcolwidth_no_wrap():
+    result = get_maxcolwidth([], False)
+    assert result is None
+
+
+def test_get_maxcolwidth_wrap_short():
+    for width in range(35, 100):
+        mock_get_terminal_size = mock.Mock(return_value=(width, 24))
+        mock_shutil = mock.Mock(get_terminal_size=mock_get_terminal_size)
+
+        with mock.patch("wily.helper.shutil", mock_shutil):
+            result = get_maxcolwidth(SHORT_DATA[0], True)
+        as_table = tabulate.tabulate(
+            tabular_data=SHORT_DATA,
+            tablefmt="grid",
+            maxcolwidths=result,
+            maxheadercolwidths=result,
+        )
+
+        line = as_table.splitlines()[0]
+        assert len(line) < width
+        assert len(line) >= width / 3
+
+
+def test_get_maxcolwidth_wrap_medium():
+    for width in range(35, 100):
+        mock_get_terminal_size = mock.Mock(return_value=(width, 24))
+        mock_shutil = mock.Mock(get_terminal_size=mock_get_terminal_size)
+
+        with mock.patch("wily.helper.shutil", mock_shutil):
+            result = get_maxcolwidth(MEDIUM_DATA[0], True)
+        as_table = tabulate.tabulate(
+            tabular_data=MEDIUM_DATA,
+            tablefmt="grid",
+            maxcolwidths=result,
+            maxheadercolwidths=result,
+        )
+
+        line = as_table.splitlines()[0]
+        print(line)
+        print(width, len(line))
+        assert len(line) < width
+        if width < 85:
+            assert len(line) >= width / 3
+
+
+def test_get_maxcolwidth_wrap_long_line_medium():
+    for width in range(35, 100):
+        mock_get_terminal_size = mock.Mock(return_value=(width, 24))
+        mock_shutil = mock.Mock(get_terminal_size=mock_get_terminal_size)
+
+        with mock.patch("wily.helper.shutil", mock_shutil):
+            result = get_maxcolwidth(LONG_LINE_MEDIUM_DATA[0], True)
+        as_table = tabulate.tabulate(
+            tabular_data=LONG_LINE_MEDIUM_DATA,
+            tablefmt="grid",
+            maxcolwidths=result,
+            maxheadercolwidths=result,
+        )
+
+        line = as_table.splitlines()[0]
+        print(line)
+        print(width, len(line))
+        assert len(line) < width
+        if width < 85:
+            assert len(line) >= width / 3
+
+
+def test_get_maxcolwidth_wrap_long():
+    for width in range(35, 290):
+        mock_get_terminal_size = mock.Mock(return_value=(width, 24))
+        mock_shutil = mock.Mock(get_terminal_size=mock_get_terminal_size)
+
+        with mock.patch("wily.helper.shutil", mock_shutil):
+            result = get_maxcolwidth(LONG_DATA[0], True)
+        as_table = tabulate.tabulate(
+            tabular_data=LONG_DATA,
+            tablefmt="grid",
+            maxcolwidths=result,
+            maxheadercolwidths=result,
+        )
+
+        line = as_table.splitlines()[0]
+        assert len(line) < width
+        if width < 290:
+            assert len(line) >= width / 3
+
+
+def test_get_maxcolwidth_wrap_huge():
+    for width in range(75, 450):
+        mock_get_terminal_size = mock.Mock(return_value=(width, 24))
+        mock_shutil = mock.Mock(get_terminal_size=mock_get_terminal_size)
+
+        with mock.patch("wily.helper.shutil", mock_shutil):
+            result = get_maxcolwidth(HUGE_DATA[0], True)
+        as_table = tabulate.tabulate(
+            tabular_data=HUGE_DATA,
+            tablefmt="grid",
+            maxcolwidths=result,
+            maxheadercolwidths=result,
+        )
+
+        line = as_table.splitlines()[0]
+        assert len(line) < width
+        if width < 220:
+            assert len(line) >= width / 3
+        else:
+            assert len(line) >= width / 4
 
 
 def test_get_style():

running wily with more than 5 metrics cause problem with printing 
when running willy with multiple metrics it causes them to overlap 
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